p-Toluenesulphonyl cyanide → HCID 57332418, compound

HRID 1503224Notes

Reaction equation

HRID 1503224 reaction equation
[N:1]([CH2:4][C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[N+:2]=[N-:3].[C:17]1([CH3:28])[CH:22]=[CH:21][C:20]([S:23]([C:26]#[N:27])(=[O:25])=[O:24])=[CH:19][CH:18]=1>>[C:10]([N:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[CH2:4][N:1]1[C:26]([S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:28])=[CH:18][CH:19]=2)(=[O:25])=[O:24])=[N:27][N:3]=[N:2]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

3

Reactant 2

HCID 87946p-Toluenesulphonyl cyanideHCID 23520181tert-Butyl (2S)-2-(azidomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 57332418HCID 57332418, compoundYield 91.2%

Procedure

(S)-2-(azidomethyl)-1-Boc-pyrrolidine (480 mg, 2.1 mmol) was added to a flask containing p-toluenesulfonyl cyanide (420 mg, 2.3 mmol) and a stir bar (no solvent). The flask was placed in a 80° C. bath and reaction proceeded for 48 hours. The reaction was concentrated in vacuo. The crude amber oil was purified by flash silica gel chromatography using a hexane/ethyl acetate gradient. The product (780 mg, 91% yield) was obtained as a colorless oil. 1H-NMR (500 MHz, CDCl3): δ 8.01 (broad d, J=18 Hz, 2H), 7.44 (m, 3H), 4.85-4.70 (m, 2H), 4.52-4.48 (m, 1H), 3.50-3.34 (m, 2H), 2.49 (s, 3H), 2.01-1.71 (m, 4H), 1.40 & 1.33 (2 s, 9H). ESI-MS (m/z) for C18H25N5O4S (exact mass 407.16): [M+H]+ calc. 408.2, obs. 408.2; [M+Na]+ calc. 430.2, obs. 430.2.

Workup

  1. customwas placed in a 80° C.
  2. customreaction
  3. concentrationThe reaction was concentrated in vacuo
  4. customThe crude amber oil was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-2b971c848b4a474a916471a38aaab5d8
Source dataset
uspto-grants-2015_12
Patent number
US09212167B2

Reaction notes

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