반응 #162093

ord-c5341cda1087455ab249852d3fe0552d

반응 방정식

CC(C)(C)OC(=O)N[C@@H]1CCCC[C@H]1C#N
tert-butyl trans-2-cyanocyclohexylcarbamate
→
CC(C)(C)OC(=O)N[C@@H]1CCCC[C@H]1CN
14d
수율 66.0%
CC(C)(C)OC(=O)N[C@@H]1CCCC[C@H]1CN
tert-butyl trans-2-(aminomethyl)cyclohexylcarbamate
수율 66.0%

반응물

CC(C)(C)OC(=O)N[C@@H]1CCCC[C@H]1C#N
tert-butyl trans-2-cyanocyclohexylcarbamate

시약

[Ni]
Ni

용매

CCO
EtOH

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    여과Filtration and evaporation of the solvent
  2. 2
    세척O-20% MeOH—CH2Cl2, gradient elution)

실험 절차

A solution of tert-butyl trans-2-cyanocyclohexylcarbamate and Raney-Ni in absolute EtOH was stirred under H2 atmosphere (50 PSI) for 24 hours. Filtration and evaporation of the solvent followed by flash chromatography (SiO2, O-20% MeOH—CH2Cl2, gradient elution) provided the target compound, 14d, as a racemic mixture of trans isomers (286 mg, 66% yield): FIA (M+H) 229.33.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08829007B2uspto-grants-2014_09