Methanol → Methyl (1S,3R)-3-aminocyclohexane-1-carboxylate

HRID 1896294Notes

Reaction equation

HRID 1896294 reaction equation
S(Cl)(Cl)=O.[NH2:5][C@@H:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([C:12]([OH:14])=[O:13])[CH2:7]1.[CH3:15]O>>[NH2:5][C@@H:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([C:12]([O:14][CH3:15])=[O:13])[CH2:7]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 7005079rac-(1R,3S)-3-aminocyclohexane-1-carboxylic acid

Product 1

HCID 68466059Methyl (1S,3R)-3-aminocyclohexane-1-carboxylateYield 90.9%

Procedure

Thionyl chloride (0.6 ml) was added to solution of cis-3-amino-cyclohexanecarboxlic acid (bought from AMRI, USA, cat.-no.: A00342, 0.50 g, 2.80 mmol) in MeOH (20 ml) at 0° C. and stirred at reflux for 12 h. The volatiles were evaporated in vacuo and the resulting residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate. The separated organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuo to afford 400 mg (90.9%) of cis-methyl 3-aminocyclohexanecarboxylate as colorless liquid.

Workup

  1. temperatureat reflux for 12 h
  2. customThe volatiles were evaporated in vacuo
  3. customthe resulting residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-4455efa5a6e94d9598cefefae388870f
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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