(+)-cis-2-Benzamidocyclohexanecarboxylic Acid → (1S,2R)-2-aminocyclohexane-1-carboxylic acid

HRID 7019Notes

Reaction equation

HRID 7019 reaction equation
C([NH:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[C:16]([OH:18])=[O:17])(=O)C1C=CC=CC=1>Cl>[NH2:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[C:16]([OH:18])=[O:17]

Participants

3

Reactant 1

HCID 1268229(+)-cis-2-Benzamidocyclohexanecarboxylic Acid

Product 1

HCID 7128325(1S,2R)-2-aminocyclohexane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of (+)-(1S,2R)-2-benzamidocyclohexanecarboxylic acid (4.0 g, 16.2 mmol, TCI chemical company) and 6 M hydrochloric acid (200 mL) was heated at reflux for 48 h. The reaction mixture was cooled to room temperature and extracted with diethyl ether (2×200 mL). The aqueous portion was concentrated in vacuo to afford (1S,2R)-2-aminocyclohexanecarboxylic acid as a white solid. The crude product was used in the next step without purification or characterization.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 h
  3. extractionextracted with diethyl ether (2×200 mL)
  4. concentrationThe aqueous portion was concentrated in vacuo

Sources & evidence

ORD record
ord-7b337e6af2f0449cad27ae97895f7ad8
Source dataset
uspto-grants-2006_08
Patent number
US07084178B2

Reaction notes

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