HCID 57832632, compound → methyl (1R,2S)-2-aminocyclohexanecarboxylate

HRID 731269Notes

Reaction equation

HRID 731269 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@@H:6]1[NH:11]C(OCC1C=CC=CC=1)=O)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@@H:6]1[NH2:11])=[O:4]

Participants

4

Reactant 1

HCID 57832632HCID 57832632, compound

Product 1

HCID 24751169methyl (1R,2S)-2-aminocyclohexanecarboxylateYield 80.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

(1R,2S)-2-Benzyloxycarbonylamino-cyclohexanecarboxylic acid methyl ester (5.78 g, 19.8 mmol) was dissolved in methanol (200 mL). 10% Palladium on charcoal (0.21 g) was added. The flask was degassed and backfilled with hydrogen gas via balloon. The mixture was stirred at 25° C. for 5 h. The mixture was passed through a plug of Celite and the filtrate was concentrated in vacuo to afford the desired product, (1R,2S)-2-amino-cyclohexanecarboxylic acid methyl ester (2.5 g, 15.9 mmol, 80%), as a clear oil. LC-MS (ESI) calcd for C8H15NO2 157.11, found 158.1 [M+H+].

Workup

  1. customThe flask was degassed
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-35cf101ae53d465d922f39c7caed6620
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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