Trans-2-(boc-amino)-cyclohexanenitrile → tert-Butyl ((1R,2S)-2-(aminomethyl)cyclohexyl)carbamate

HRID 74911Notes

Reaction equation

HRID 74911 reaction equation
[C:1]([C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])#[N:2]>CCO.[Ni]>[NH2:2][CH2:1][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15]

Participants

4

Reactant 1

HCID 68008329Trans-2-(boc-amino)-cyclohexanenitrile

Product 1

HCID 68007523tert-Butyl ((1R,2S)-2-(aminomethyl)cyclohexyl)carbamateYield 66%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-c5341cda1087455ab249852d3fe0552d
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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