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

HRID 2200373Notes

Reaction equation

HRID 2200373 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][C@@H:5]([C:8]([OH:10])=[O:9])[CH2:4]1.S(Cl)(Cl)=O.[CH3:15]O>>[CH3:15][O:9][C:8]([C@H:5]1[CH2:6][CH2:7][C@@H:3]([NH2:2])[CH2:4]1)=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 54611811(1R,3S)-3-aminocyclopentane-1-carboxylic acid hydrochloride

Product 1

HCID 45089124Methyl (1S,3R)-3-aminocyclopentane-1-carboxylateYield 98%

Procedure

To a solution of (1R,3S)-3-aminocyclopentanecarboxylic acid hydrochloride (2.5 g, 15.09 mmol) in dry methanol (10 ml) under N2 at 0° C. was added thionyl chloride (5.51 ml, 75 mmol) dropwise. The reaction mixture was slowly warmed to room temperature and stirred overnight. The reaction was concentrated in vacuo. The resultant residue was washed with anhydrous diethyl ether (3×30 ml) and dried under high vacuum to afford of (1S,3R)-3-aminocyclopentanecarboxylic acid methyl ester (2.65 g 98%) as the hydrochloride salt that was used in a subsequent reaction without purification.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. washThe resultant residue was washed with anhydrous diethyl ether (3×30 ml)
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-6353dbb7a62d442189c700f6d6bd7b85
Source dataset
uspto-grants-2016_06
Patent number
US09359367B2

Reaction notes

Loading…