tert-Butyl[(1R*,3R*,4R*)-4-azido-3-methylcyclohexyl]carbamate → tert-butyl[(1R*,3R*,4R*)-4-amino-3-methylcyclohexyl]carbamate

HRID 1423414Notes

Reaction equation

HRID 1423414 reaction equation
[N:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][C@H:5]1[CH3:18])=[N+]=[N-]>CO.[Pd]>[NH2:1][C@@H:4]1[CH2:9][CH2:8][C@@H:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16])[CH2:6][C@H:5]1[CH3:18]

Participants

4

Reactant 1

HCID 131732233tert-Butyl[(1R*,3R*,4R*)-4-azido-3-methylcyclohexyl]carbamate

Product 1

HCID 131116877tert-butyl[(1R*,3R*,4R*)-4-amino-3-methylcyclohexyl]carbamateYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl [(1R*,3R*,4R*)-4-azido-3-methylcyclohexyl]carbamate (example C10; 1.2 g; 4.7 mmol) is dissolved in MeOH (20.0 mL) and pressure hydrogenated over Pd (10% on charcoal; 0.1 g) at 20 bar and ambient temperature over night. After filtration through a pad of celite the solvent is removed under reduced pressure to yield 1.0 g of the title compound as off-white solid.

Workup

  1. filtrationAfter filtration through a pad of celite the solvent
  2. customis removed under reduced pressure

Sources & evidence

ORD record
ord-9b17bb2525be4f339de25da92900d710
Source dataset
uspto-grants-2015_01
Patent number
US08927557B2

Reaction notes

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