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

反応式

[NH2:1][C@H:2]1[CH2:6][CH2:5][C@@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.S(Cl)([Cl:12])=O.[CH3:14]O>>[ClH:12].[NH2:1][C@H:2]1[CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH3:14])=[O:8])[CH2:3]1

参加物

反応物 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 1502035Cyclopentanecarboxylic acid, 3-amino-, (1R,3S)-rel- (9CI)

生成物 1

HCID 57463822methyl (1R,3S)-3-aminocyclopentane-1-carboxylate hydrochloride

反応条件

温度: 0 °C

実験手順

A suspension of (1R,3S)-3-aminocyclopentanecarboxylic acid (500 mg, 3.8 mmol) in methanol (10 mL) was stirred at 0° C. and thionyl chloride (1.40 mL, 19.3 mmol) was added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. The resulting clear solution was evaporated, azeotroped with methanol (2×5 mL), air-dried and the title compound obtained as a white powder (680 mg).