Supporting Information for Boiling Water-Catalyzed Neutral ... · Boiling Water-Catalyzed Neutral and Selective N-Boc Deprotection Jia Wang, Yan-Liang Liang, Jin Qu* The State Key

S1

Supporting Information for

Boiling Water-Catalyzed Neutral and Selective N-Boc

Deprotection

Jia Wang, Yan-Liang Liang, Jin Qu*

The State Key Laboratory of Elemento-organic Chemistry,

Nankai University, Tianjin 300071, P. R. China

Fax: +86-(022)-23499247 and E-mail:[email protected]

Table of Contents

General.............................................................................................................................................2

General Procedure for N-Boc Deprotection Reaction in Boiling Water ....................................2

1H NMR Studies of the Deprotection of N-Boc-benzotriazole in D2O at 60oC ..........................3

Analytical Data for Compounds in Table 1 ..................................................................................4



Selected NMR Spectra ..................................................................................................................14

References ......................................................................................................................................18

Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2009

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General

All reactions were carried out in aerial atmosphere, unless otherwise mentioned. Water was

purchased from Watson water or from Milli-Q® Ultrapure Water Purification System. Flash chromatography was performed on silica gel columns (200 – 300 mesh). All of the compounds were characterized by 1H NMR and 13C NMR. 1H NMR spectra were recorded at 300 MHz, 400 MHz or 600 MHz; 13C NMR were recorded at 75 MHz, 100 MHz or 150 MHz. Peaks recorded are relative to internal standards: TMS (δ = 0.00) for 1H and CDCl3 (δ = 77.00) for 13C spectra.

General Procedure for N-Boc Deprotection Reaction in Boiling Water

In a 50 mL round bottle flask filled with 20 mL of water, tert-butyl 3–(hydroxymethyl)

phenylcarbamate (223 mg, 1 mmol) was added. Then the flask topped with a condenser was dipped in a 110℃ oil bath. TLC was used to monitor the progress of the reaction. The reaction mixture was cooled down after 1.5 h and was extracted with ethyl acetate (40 mL×3). The extract was washed with brine, dried over anhydrous Na2SO4, and then concentrated in vacuum. The residue was purified by column chromatography on silica gel with ethyl acetate/petroleum ether (1:1, v/v) to afford the free amine as a colorless solid (120 mg, yield 98%, for most of cases, no further purification is needed). 1H NMR (400 MHz, CDCl3) δ 7.42 (s, 1H), 7.21–7.24 (m, 2H), 7.03 (d, J = 6.8 Hz, 1H), 6.56 (br s, 1H, NH), 4.65 (s, 2H), 1.95 (br s, 1H, OH), 1.51 (s, 9H)

Most of the substrate was insoluble in water at room temperature, but it became partially

soluble or completely miscible when temperature was raised above 60°C. For very sticky Nα,Nind-diBoc-tryptamine, the substrate was firstly dissolved in 1 mL of 1,4-dioxane and then 19 mL of water was added. We note that most organic compounds containing one or more hydrogen-bond-forming functional groups should have good solubility in hot water (60−100°C).


S3

1H NMR Studies of the Deprotection of N-Boc-benzotriazole in D2O at 60oC

The white solid of N-Boc-benzotriazole (100 mg) and 500 μL of D2O were placed in

an NMR tube and were sonicated for 1 minute at room temperature. There is no signal

in the 1H NMR spectrum recorded because N-Boc-benzotriazole is not soluble in pure

water at room temperature. The NMR tube was then immersed into a 60oC water bath

for 4 min (shake the NMR tube occasionally) and then was cooled down in an ice bath.

The peaks of N-Boc-benzotriazole appear in the 1H NMR spectrum were recorded

because N-Boc-benzotriazole is partially soluble in water after heating (in order to

insure that the signals in 1H NMR spectrum belong to the starting material, a 13C

NMR spectrum of the 4 min sample was also taken and compared with the 13C NMR

spectrum of N-Boc-benzotriazole taken in CDCl3). The high-field singlet attributes to

the t-butanol formed in the reaction. Similarly, the NMR tube was heated for another

4 minutes and was cooled down before the 1H NMR spectrum was recorded. On the 1H NMR spectrum, the signals of the product rise while the signals of the starting

material fall down. After the reaction finished (16 min), 20 mg of authentic t-butanol

was added in the NMR tube and it is found that the high field singlet do not split

which means it is the signal from t-butanol.

4 min

8 min12 min16 min

20 mg t -BuOH added

CH3 in t-BuOH

before heating

solvent peak of D2O

N

N

N

OO

H2O

NH

N

N

60oC


S4

Analytical Data for Compounds in Table 1

tert–Butyl 1H–imidazole–1–carboxylate 1

N

N

Boc

Table 1 - Entry 1

1H NMR (400 MHz, CDCl3) δ 8.08 (d, J = 2.4 Hz, 1H), 7.38 (s, 1H), 7.03 (d, J = 2.4 Hz, 1H), 1.63 (s, 9H) tert–Butyl 1H–pyrazole–1–carboxylate 2

NNBoc

Table 1 - Entry 2 1H NMR (400 MHz, CDCl3) δ 8.11 (d, J = 2.4 Hz, 1H), 7.72 (s, 1H), 6.39 (t, J = 2.8 Hz, 1H), 1.66 (s, 9H) tert–Butyl 1H–benzo[d]imidazole–1–carboxylate 3

N

N

BocTable 1 - Entry 3

1H NMR (600 MHz, CDCl3) δ 8.43 (s, 1H), 7.99 (d, J = 7.8 Hz, 1H), 7.79 (d, J = 7.8 Hz, 1H), 7.34–7.39 (m, 2H), 1.70 (s, 9H) tert–Butyl 1H–benzo[d][1,2,3]triazole–1–carboxylate 4

NN

NBoc

Table 1 - Entry 4 1H NMR (600 MHz, CDCl3) δ 8.12 (d, J = 8.4 Hz, 1H), 8.07 (d, J = 8.4 Hz, 1H), 7.63 (t, J = 7.8 Hz, 1H), 7.48 (t, J = 7.8 Hz, 1H), 1.77 (s, 9H)


S5

tert–Butyl 1H–indole–1–carboxylate 5

NBoc

Table 1 - Entry 5

1H NMR (600 MHz, CDCl3) δ 8.15 (m, 1H), 7.59 (s, 1H), 7.55 (d, J = 7.8 Hz, 1H), 7.30 (d, J = 7.8 Hz, 1H), 7.22 (m, 1H), 6.56 (s, 1H), 1.67 (s, 9H) tert–Butyl 1H–pyrrolo[2,3–b]pyridine–1–carboxylate 6

N NBoc

Table 1 - Entry 6

1H NMR (400 MHz, CDCl3) δ 8.51 (dd, J = 1.6, 4.8 Hz, 1H), 7.87 (dd, J = 1.6, 7.6 Hz, 1H), 7.64 (d, J = 4.0 Hz, 1H), 7.18 (dd, J = 4.8, 7.6 Hz, 1H), 6.50 (d, J = 4.0 Hz, 1H), 1.67 (s, 9H) tert–Butyl 3–acetyl–1H–indole–1–carboxylate 7

NBoc

Ac

Table 1 - Entry 7

1H NMR (600 MHz, CDCl3) δ 8.37 (m, 1H), 8.23 (s, 1H), 8.12 (m, 1H), 7.37 (m, 2H), 2.57 (s, 3H, CH3), 1.72 (s, 9H)


S6


tert–Butyl phenylcarbamate 8

Table 2 - Entry 1

HN Boc

1H NMR (300 MHz, CDCl3) δ 7.39 (d, J = 8.0 Hz, 2H), 7.32 (t, J = 8.0 Hz, 2H), 7.03 (t, J = 7.2 Hz, 1H), 6.48 (s, 1H, NH), 1.52 (s, 9H) tert–Butyl p–tolylcarbamate 9

Table 2 - Entry 2

HN Boc

1H NMR (400 MHz, CDCl3) δ 7.23 (d, J = 8.0 Hz, 2H), 7.09 (d, J = 8.4 Hz, 2H), 6.42 (br s, 1H, NH), 2.29 (s, 3H), 1.51 (s, 9H) tert–Butyl 4–chlorophenylcarbamate 10

Table 2 - Entry 3

HN BocCl

1H NMR (400 MHz, CDCl3) δ 7.31 (d, J = 8.8 Hz, 2H), 7.24 (d, J = 9.2 Hz, 2H), 6.53 (br s, 1H, NH), 1.51 (s, 9H) tert–Butyl 4–bromophenylcarbamate 9

Table 2 - Entry 4

HN BocBr

1H NMR (600 MHz, CDCl3) δ 7.38 (d, J = 8.4 Hz, 2H), 7.25 (d, J = 8.4 Hz, 2H), 6.48 (br s, 1H, NH), 1.53 (s, 9H) tert–Butyl 4–hydroxyphenylcarbamate 9


S7

Table 2 - Entry 5

HN BocHO

1H NMR (600 MHz, CDCl3) δ 7.17 (d, J = 7.2 Hz, 2H), 6.73 (d, J = 7.2 Hz, 2H), 6.34 (br s, 1H, NH), 5.27 (br s, 1H, OH), 1.51 (s, 9H) tert–Butyl 3–hydroxyphenylcarbamate 11

Table 2 - Entry 6

HO

NH Boc

1H NMR (400 MHz, CDCl3) δ 7.11 (m, 2H), 6.72 (d, J = 7.6 Hz, 1H), 6.52 (t, J = 8.0 Hz, 2H), 5.39 (br s, 1H), 1.52 (s, 9H) tert–Butyl 4–methoxyphenylcarbamate 1

Table 2 - Entry 7

HN BocO

1H NMR (600 MHz, CDCl3) δ 7.25 (d, J = 9.0 Hz, 2H), 6.83 (d, J = 9.0 Hz, 2H), 6.35 (br s, 1H, NH), 3.78 (s, 3H), 1.51 (s, 9H) tert–Butyl 4–acetoxyphenylcarbamate 12

Table 2 - Entry 8

AcOHN Boc

1H NMR (300 MHz, CDCl3) δ 7.36 (d, J = 9.0 Hz, 2H), 7.01 (d, J = 8.7 Hz, 2H), 6.49 (br s, 1H, NH), 2.28 (s, 3H), 1.51 (s, 9H); 13C NMR (75 MHz, CDCl3) δ 188.62, 152.69, 146.04, 136.01, 121.93, 119.42, 80.65, 28.31, 21.04 tert–Butyl 3–(hydroxymethyl)phenylcarbamate 13


S8

Table 2 - Entry 9

OH

NH Boc

1H NMR (400 MHz, CDCl3) δ 7.42 (s, 1H), 7.21–7.24 (m, 2H), 7.03 (d, J = 6.8 Hz, 1H), 6.56 (br s, 1H, NH), 4.65 (s, 2H), 1.95 (br s, 1H, OH), 1.51 (s, 9H) tert–Butyl 4–acetylphenylcarbamate 14

Table 2 - Entry 10

AcHN Boc

1H NMR (300 MHz, CDCl3) δ 7.81 (d, J = 8.7 Hz, 2H), 7.43 (d, J = 8.1 Hz, 2H), 6.55 (s, 1H, NH), 2.47 (s, 3H), 1.41 (s, 9H); 13C NMR (100 MHz, CDCl3) δ 197.12, 152.31, 143.26, 131.36, 129.67, 117.34, 80.88, 28.09, 26.20 tert–Butyl 4–nitrophenylcarbamate 1

Table 2 - Entry 11

HN BocO2N

1H NMR (400 MHz, CDCl3) δ 8.18 (d, J = 9.2 Hz, 2H), 7.54 (d, J = 9.2 Hz, 2H), 6.96 (br s, 1H, NH), 1.54 (s, 9H) tert–Butyl 4–(dimethylamino)phenylcarbamate 15

Table 2 - Entry 12

HNN Boc

1H NMR (400 MHz, CDCl3) δ 7.21 (d, J = 6.4 Hz, 2H), 6.70 (t, J = 6.4 Hz, 2H), 6.25 (br s, 1H, NH), 2.89 (s, 6H), 1.50 (s, 9H)


S9


tert–Butyl Butylcarbamate 3

NH

Boc

Table 3 - Entry 1 - Substrate

1H NMR (400 MHz, CDCl3) δ 4.52 (s, 1H, NH), 2.74-2.75 (m, 2H), 1.08 (s, 9H), 1.07-1.11 (m,

2H), 0.95-1.01 (m, 2H), 0.55 (t, J = 0.8 Hz, 3H)

tert–Butyl 5–hydroxypentylcarbamate 16


BocHN OH

1H NMR (600 MHz, CDCl3) δ 4.68 (s, 1H, NH), 3.64 (t, J = 6.0 Hz, 3H), 3.12 (br, 2H), 2.08–2.19 (m, 1H), 1.57–1.60 (m, 2H), 1.50–1.52 (m, 2H), 1.44 (s, 9H), 1.38–1.41 (m, 2H); 13C NMR (150 MHz, CDCl3) δ 156.08, 79.06, 62.53, 40.36, 32.19, 29.79, 28.37, 22.87 tert–Butyl 2–hydroxycyclohexylcarbamate 17


HN

OH

Boc

trans

1H NMR (400 MHz, CDCl3) δ 4.61 (br s, 1H), 3.30 (br s, 3H), 1.95–2.05 (m, 2H), 1.68–1.70 (m, 2H), 1.45 (s, 9H), 1.12–1.30 (m, 4H); 13C NMR (100 MHz, CDCl3) δ 157.12, 79.85, 75.13, 56.52, 34.08, 31.72, 28.31, 24.64, 24.00 tert–Butyl 4–hydroxypiperidine–1–carboxylate 18


S10


N

OH

Boc

1H NMR (600 MHz, CDCl3) δ 3.80–3.88 (m, 3H), 3.03 (m, 2H), 1.83–1.88 (m, 2H), 1.67 (br s, 1H, OH), 1.46 (s, 9H), 1.39–1.54 (m, 2H); 13C NMR (150 MHz, CDCl3) δ 154.80, 79.52, 67.71, 41.23, 34.14, 28.40 tert-Butyl 2-oxopiperidine-1-carboxylate 19


N

O

Boc

1H NMR (600 MHz, CDCl3) δ 3.52−3.58 (m, 2H), 2.35−2.46 (m, 2H), 1.67−1.77 (m, 4H), 1.42 (s, 9H); 13C NMR (150 MHz, CDCl3) δ 171.15, 152.45, 82.54, 46.12, 34.68, 27.79, 25.57, 20.28 tert–Butyl (S)–1–(methoxycarbonyl)ethylcarbamate 20

1H NMR (400 MHz, CDCl3) δ 5.05 (br, 1H), 4.32 (m, 1H), 3.75 (s, 3H), 1.45 (s, 9H), 1.38 (d, J = 6.4 Hz, 3H); 13C NMR (150 MHz, CDCl3) δ 173.80, 155.06, 79.77, 52.24, 49.10, 28.26, 18.59 tert–Butyl (S)–1–(cyclohexylcarbamoyl)–2–hydroxyethylcarbamate 21


HN

OH

NH

O

Boc

1H NMR (300 MHz, CDCl3) δ 6.72 (s, 1H, NH), 5.70 (s, 1H), 4.04–4.13 (m, 2H), 3.70–3.76 (m, 2H), 3.64 (s, 1H), 1.46 (s, 9H), 1.17–2.07 (m, 10H); 13C NMR (75 MHz, CDCl3) δ 170.45, 156.33, 80.47, 62.85, 54.81, 54.76, 48.13, 32.68, 28.26, 25.43, 25.51


HN

O

O

Boc


S11

(S)–2–amino–N–cyclohexyl–3–hydroxypropanamide 22

Table 3 - Entry 8 - Product

H2N

OH

NH

O

1H NMR (300 MHz, CDCl3) δ 7.37–7.39 (br s, 1H), 3.72–3.82 (br, 3H), 3.43 (t, J = 4.8 Hz, 1H), 2.62 (br s, 4H), 1.13–2.05 (m, 9H); 13C NMR (75 MHz, CDCl3) δ 172.63, 65.30, 55.86, 47.81, 32.98, 32.87, 25.46, 24.72 tert–Butyl 2–(1–(tert–butoxycarbonyl)–1H–imidazol–5–yl)ethylcarbamate 23

Table 3 - Entry 9 - SubstrateN

N

HN BocBoc

1H NMR (400 MHz, CDCl3) δ 8.01 (s, 1H), 7.14 (s, 1H), 5.02 (br s, 1H, NH), 3.43 (t, J = 6.3 Hz, 2H), 2.74 (t, J = 6.6 Hz, 2H), 1.61 (s, 9H), 1.44 (s, 9H); 13C NMR (100 MHz, CDCl3) δ 155.89, 146.99, 141.20, 136.78, 113.65, 85.36, 79.04, 39.80, 28.37, 28.29, 27.86 tert–Butyl 2–(1H–imidazol–5–yl)ethylcarbamate 24

Table 3 - Entry 9 - ProductN

HN

HN Boc

1H NMR (400 MHz, CDCl3) δ 11.07 (s, 1H), 7.53 (s, 1H), 6.74 (s, 1H), 5.35 (s, 1H, NH), 3.30 (s, 2H), 2.72 (s, 2H), 1.33 (s, 9H); 13C NMR (150 MHz, CDCl3) δ 156.06, 134.72, 116.77, 99.80, 78.92, 40.20, 28.16, 27.24 tert–Butyl 2–(1–(tert–butoxycarbonyl)–1H–indol–3–yl)ethylcarbamate 25


N

NH

Boc

Boc


S12

1H NMR (600 MHz, CDCl3) δ 8.14 (d, J = 8.0 Hz, 1H), 7.52 (d, J = 7.8 Hz, 1H), 7.41 (s, 1H), 7.30 (t, J = 7.2 Hz, 1H), 7.21 (t, J = 7.2 Hz, 1H), 4.85 (br s, 1H, NH), 3.44 (s, 2H), 2.87 (s, 2H), 1.65 (s, 9H), 1.43 (s, 9H); 13C NMR (150 MHz, CDCl3) δ 155.77, 149.49, 135.39, 130.29, 124.23, 122.92, 122.28, 118.77, 117.65, 115.08, 83.22, 78.90, 40.07, 29.50, 28.22, 27.99 tert–Butyl 2–(1H–indol–3–yl)ethylcarbamate 26

NH

NH O

O

Table 3 - Entry 10 - Product

1H NMR (600 MHz, CDCl3) δ 8.08 (s, 1H), 7.61 (d, J = 7.8 Hz, 1H), 7.37 (d, J = 7.8 Hz, 1H), 7.20 (t, J = 7.2 Hz, 1H), 7.12 (t, J = 7.8 Hz, 1H), 7.03 (s, 1H), 4.62 (s, 1H), 3.47 (d, J = 6.0 Hz, 2H), 2.96 (t, J = 6.0 Hz, 2H), 1.44 (s, 9H); 13C NMR (150 MHz, CDCl3) δ 156.06, 136.43, 127.37, 122.01, 119.30, 118.72, 112.99, 112.93, 111.19, 79.24, 41.07, 28.41, 25.81 (S)-tert-Butyl 2-(butyl-tert-Butoxycarbonylcarbamoyl)pyrrolidine-1-carboxylate

NN

OBoc

Boc

Table 3 - Entry 11 - Substrate 1H NMR (600 MHz, CDCl3) δ 5.18-5.22 (m, 1H), 3.58-3.75 (m, 3H), 3.42-3.50 (m, 1H), 2.32 (s, 1H), 1.86-1.95 (m, 3H), 1.56 (s, 5H), 1.54 (s, 4H), 1.47 (s, 4H), 1.40 (s, 5H), 1.27-1.36 (m, 4H), 0.91-0.96 (m, 3H); 13C NMR (150 MHz, CDCl3) δ 175.73, 175.39, 154.10, 153.42, 152.79, 152.59, 82.73, 82.48, 78.90, 78.87, 61.01, 60.54, 46.65, 46.35, 44.26, 44.21, 30.91, 30.57, 30.40, 30.25, 28.18, 28.00, 27.69, 23.28, 27.72, 19.78, 19.73, 13.53, 13.50 (cis/trans=1:1); LRMS (ESI) [M+H]+ m/z 371.0; HRMS (ESI) for C19H34N2O5: Calcd for [M+H]+ m/z 371.2573, found 371.2579. (S)-tert-Butyl 2-(butylcarbamoyl)pyrrolidine-1-carboxylate 27

N

HN

OBocTable 3 - Entry 11 - Product


S13

1H NMR (600 MHz, CDCl3) δ 6.85 (s, 0.5H), 6.42 (s, 0.5H), 3.93-4.00 (m, 1H), 2.93-3.19 (m, 4H), 1.60-1.99 (m, 4H), 1.19 (s, 9H), 1.08-1.09 (m, 4H), 0.65 (m, 3H); 13C NMR (150 MHz, CDCl3) δ 171.58, 171.55, 155.08, 154.11, 99.70, 79.59, 60.63, 59.77, 46.54, 38.51, 31.23, 31.19, 31.06, 30.72, 27.83, 24.02, 23.20, 19.48, 13.19 (cis/trans=1:1)


S14

Selected NMR Spectra

tert–Butyl 2–(1H–imidazol–5–yl)ethylcarbamate 1H NMR

ppm (t1)0.05.010.0

0

10000

20000

30000

40000

50000

60000

11.9

02

7.52

4

6.76

5

5.37

9

3.33

4

2.74

3

1.35

3

1.00

0.99

1.00

0.90

2.03

2.01

9.04

HNN

HNBoc

1H NMR, 600MHz, CDCl3

tert–Butyl 2–(1H–imidazol–5–yl)ethylcarbamate 13C NMR

ppm (t1)050100150

0

10000

20000

30000

40000

50000

60000

156.

061

134.

722

116.

765

99.7

96

78.9

24

77.2

1277

.000

76.7

88

40.2

01

28.1

5927

.244

HNN

HNBoc

13C NMR, 150MHz, CDCl3

solvent peak solvent peak


S15

tert–Butyl 2–(1H–indol–3–yl)ethylcarbamate 1H NMR

ppm (t1)0.05.010.0

0

50000

10000

15000

20000

250008.

372

8.36

68.

362

8.36

08.

356

8.35

48.

351

8.34

88.

347

8.34

38.

342

7.63

8

7.38

77.

272

7.23

77.

227

7.16

07.

149

7.01

1

4.67

14.

668

4.66

64.

664

4.66

34.

655

4.64

2

3.49

3

2.98

72.

979

1.48

5

9.00

0.88

1.00

1.021.001.021.00

0.87

2.02

2.04

NH

NH

Boc

1H NMR,600MHz,CDCl3

tert–Butyl 2–(1H–indol–3–yl)ethylcarbamate 13C NMR

ppm (t1)050100150200

0

10000

20000

30000

40000

50000

60000

156.

062

136.

426

127.

368

122.

009

119.

298

118.

718

112.

986

112.

930

111.

188

79.2

4277

.212

77.0

0076

.788

41.0

72

28.4

0525

.811

NH

NH

Boc

13C NMR,150MHz,CDCl3


S16

(S)-tert-Butyl 2-(butyl-tert-Butoxycarbonylcarbamoyl)pyrrolidine-1-carboxylate 1H NMR

ppm (t1)1.02.03.04.05.0

0

50000

10000

5.22

15.

207

5.19

05.

176

4.14

84.

136

4.12

44.

112

3.74

73.

732

3.71

13.

699

3.68

43.

669

3.65

83.

646

3.63

53.

626

3.60

43.

595

3.58

23.

504

3.49

33.

480

3.47

73.

466

3.44

73.

434

3.42

22.

323

2.31

8

2.05

01.

952

1.93

81.

926

1.89

41.

873

1.86

81.

861

1.56

11.

535

1.46

81.

400

1.36

01.

349

1.33

81.

327

1.31

51.

271

0.96

00

925

091

3

3.05

1.00

3.08

1.00

0.96

2.88

4.02

4.994.064.004.99

NN

O

BocBoc

1H NMR, 600MHz, CDCl3

(S)-tert-Butyl 2-(butyl-tert-Butoxycarbonylcarbamoyl)pyrrolidine-1-carboxylate 13C NMR

ppm (t1)050100150200

0

10000

20000

30000

40000

50000

60000

70000

80000175.

727

175.

388

154.

095

153.

418

152.

789

152.

593

82.7

2982

.482

78.9

0278

.866

77.2

1377

.000

76.7

8761

.010

60.5

3546

.653

46.3

4944

.263

44.2

1030

.905

30.5

7430

.404

30.2

4928

.184

27.9

9527

.687

23.2

8122

.724

19.7

7719

732

NN

O

BocBoc

13C NMR, 150MHz, CDCl3


S17

(S)-tert-Butyl 2-(butylcarbamoyl)pyrrolidine-1-carboxylate 1H NMR

ppm (t1)0.05.0

0

10000

20000

30000

40000

6.84

7

6.42

0

3.99

93.

932

3.19

23.

053

3.04

93.

007

2.99

12.

929

1.98

6

1.90

31.

789

1.76

81.

665

1.59

51.

189

1.08

41.

075

0.64

7

3.00

0.97

4.08

4.07

9.003.99

0.46

0.42

NNH

O

Boc1H NMR, 600MHz, CDCl3

(S)-tert-Butyl 2-(butylcarbamoyl)pyrrolidine-1-carboxylate 13C NMR

ppm (t1)050100150

0

50000

10000

15000

20000

25000

171.

584

171.

554

155.

076

154.

105

99.6

98

79.5

9277

.213

77.0

0076

.786

60.6

3259

.768

46.5

3638

.511

31.2

3331

.194

31.0

5830

.718

27.8

2624

.020

23.1

9619

.482

13.1

87

NNH

O

Boc13C NMR, 150MHz, CDCl3


S18

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