Methanol → methyl (1R,2S)-2-aminocyclohexanecarboxylate

HRID 724291Notes

Reaction equation

HRID 724291 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[C:8]([OH:10])=[O:9].[CH3:11]O>>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[C:8]([O:10][CH3:11])=[O:9]

Participants

3

Reactant 2

HCID 887MethanolHCID 2724639(1R,2S)-2-Aminocyclohexane-1-carboxylic acid

Product 1

HCID 24751169methyl (1R,2S)-2-aminocyclohexanecarboxylate

Procedure

cis-2-Amino-1-cyclohexane carboxylic acid (2500 mg, 17.5 mmol) was suspended in methanol (30 ml) at 0° C. Gaseous hydrochloric acid was bubbled through the suspension for 10 minutes. The reaction was allowed to reach room temperature then stirred under nitrogen for 1 h and the solvent removed under reduced pressure. The residue was azeotroped with diethyl ether (2×20 ml) and dried to give the title compound as a solid.

Workup

  1. customGaseous hydrochloric acid was bubbled through the suspension for 10 minutes
  2. customto reach room temperature
  3. customthe solvent removed under reduced pressure
  4. customThe residue was azeotroped with diethyl ether (2×20 ml)
  5. customdried

Sources & evidence

ORD record
ord-d721387cdc794cd9bc45f94ab6ccd58f
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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