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

반응식

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]

참가 물질

반응물 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 54611811(1R,3S)-3-aminocyclopentane-1-carboxylic acid hydrochloride

생성물 1

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

실험 절차

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.