Ethyl (3S)-piperidine-3-carboxylate → HCID 57937302, compound

HRID 1435503Notes

Reaction equation

HRID 1435503 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:19]=[CH:20][C:21]([S:23](Cl)(=[O:25])=[O:24])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:27]1[CH2:32][CH2:31][CH2:30][C@H:29]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:28]1>>[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]2)[C:8]2[CH:19]=[CH:20][C:21]([S:23]([N:27]3[CH2:32][CH2:31][CH2:30][C@H:29]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:28]3)(=[O:25])=[O:24])=[CH:22][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 187784Ethyl (3S)-piperidine-3-carboxylateHCID 579372942-tert-Butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 57937302HCID 57937302, compound

Procedure

2-tert-Butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride (1.2 g, 2.9 mmol) was slowly added to a solution of ethyl (3S)-piperidine-3-carboxylate (0.7 g, 4.4 mmol) and DIPLA (2.6 mL, 14 mmol) in DCL (50 mL) at 80° C. The reaction mixture was stirred for 1 h and the solvent was concentrated. The product was purified by MPLC on silica gel using 60-90% EtOAc/Heptane to provide the title compound as white solid. Yield: 1.5 g (96%); MS (ESI) (M+H)+=526.0.

Workup

  1. concentrationthe solvent was concentrated
  2. customThe product was purified by MPLC on silica gel using 60-90% EtOAc/Heptane

Sources & evidence

ORD record
ord-32630eaa6b304bb3ab7cbd51cfd69eea
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

Loading…