Ethyl Acetate → (1R,2R)-trans-N-Boc-2-Aminocyclohexanol

HRID 2421062Notes

Reaction equation

HRID 2421062 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[O:14]CC1C=CC=CC=1)([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C>[Pd].CO>[C:1]([O:5][C:6](=[O:22])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[OH:14])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 59025417(1R,2R)-N-tert-Butoxycarbonyl-2-benzyloxycyclohexylamine

Product 1

HCID 10921888(1R,2R)-trans-N-Boc-2-AminocyclohexanolYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (1R,2R) (2-benzyloxycyclohexyl) carbamic acid tert-butyl ester (7 g, 23 mmoles) in a 9:1 mixture of ethyl acetate and methanol (80 mL), 10% Pd—C (1.13 g) was added and hydrogenated at 35 psi for 4 h. The catalyst was removed by filtration through a celite pad. The filtrate was concentrated to give the title compound as an oil (4.7 g, 95%). MS: (M+1): 215.95

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration through a celite pad
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8d41d15aa7ee4e67ac9bb40e6daae99f
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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