p-Toluenesulphonyl cyanide → HCID 57332418, compound

HRID 1363471Notes

Reaction equation

[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([S:7]([C:10]#[N:11])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:13]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[CH2:25][N:26]=[N+:27]=[N-:28])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>>[C:13]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[CH2:25][N:26]1[C:10]([S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:12])=[CH:6][CH:5]=2)(=[O:8])=[O:9])=[N:11][N:28]=[N:27]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

Reactant 2

HCID 87946p-Toluenesulphonyl cyanide

HCID 23520181tert-Butyl (2S)-2-(azidomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 57332418HCID 57332418, compoundYield 84%

Conditions

Temperature: 80 °C

Procedure

A sealed tube was charged with p-toluenesulfonyl cyanide (5.0 g, 22.1 mmol) and (S)-Boc-2-azido methyl pyrrolidine (1) [Black, J.; Brown, A. D.; Erizabet C. L.; Smith, J. D,; Mckelloy, A. B. 2000 JP2000063380/] (4.0 g, 22.1 mmol). The mixture was stirred at 80° C. for 40 hrs. The crude product was purified on flash silica gel column with (Hexane:EtOAc=1:1) to furnish 2 (7.6 g, 84%) as colorless foam. [α]D−11.7 (c 0.64, CHCl3). 1H NMR (400 MHz, CD3OD, −20° C., rotamers 6:4): δ 1.20 & 1.35 (s, 9H), 1.83 & 2.01 (m, 4H), 2.50 (s, 3H) 3.40 & 3.45 (m, 2H), 4.40 & 4.43 (m, 1H), 4.71 & 4.82 (m, 2H), 7.50 & 7.70 (d, J=8 Hz, 2H), 8.00 & 8.40 (d, J=8 Hz, 2H); 13C NMR (75 MHz, CDCl3): δ 22.0, 23.7, 28.4, 46.5, 52.1, 56.1, 76.9, 80.6, 129.4, 134.4, 147.4, 154.4, 154.8, 155.5; IR (film): 2976, 1693, 1392, 815, 704 cm−1; MS: (ESI) [M+1]+ 408.2.

Workup

customThe crude product was purified on flash silica gel column with (Hexane:EtOAc=1:1)

Sources & evidence

ORD record: ord-ee4006defa75468eac8d308ecb2e7c3c
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884211B2

Reaction notes

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