methyl (1R,2S)-2-benzyloxycarbonylamino-1-ethyl-cyclohexanecarboxylate → (1R,2S)-methyl 2-amino-1-ethylcyclohexanecarboxylate

HRID 74956Notes

Reaction equation

HRID 74956 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@@:13]1([CH2:22][CH3:23])[C:18]([O:20][CH3:21])=[O:19])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][C@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@@:13]1([CH2:22][CH3:23])[C:18]([O:20][CH3:21])=[O:19]

Participants

4

Reactant 1

HCID 68008489methyl (1R,2S)-2-benzyloxycarbonylamino-1-ethyl-cyclohexanecarboxylate2×

Product 1

HCID 68008279(1R,2S)-methyl 2-amino-1-ethylcyclohexanecarboxylateYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl (1R,2S)-2-benzyloxycarbonylamino-1-ethyl-cyclohexanecarboxylate, 38b, (0.27 g, 0.85 mmol) in MeOH (7.5 mL) was purged with nitrogen and a catalytic amount of Pd (5% Pd on carbon) was added. The solution was placed under H2 atmosphere and stirred at room temperature. After 1 hour, the MeOH solution suspension was filtered through celite, and concentrated in vacuo to provide the desired product (138 mg, 88% yield). The material was diluted in acetonitrile and concentrated to remove residual methanol.

Workup

  1. filtrationthe MeOH solution suspension was filtered through celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-96968fa4cf834f4baa89875cd2e9c77b
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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