Ammonium Hydroxide → cis-3-(Boc-amino)cyclopentanecarboxamide

Participants

Reaction Steps

To a solution of racemic (1R,3S)-3-(tert-butoxycarbonylamino)cyclopentane-carboxylic acid (AMRI, 3.9 g, 17.0 mmol) in dichloromethane (100 mL) was added 1-hydroxybenzotriazole monohydrate (3.1 g, 20.4 mmol), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (4.7 g, 24.7 mmol) and ammonium hydroxide (19.9 g, 170 mmol). The reaction mixture was stirred at room temperature for 16 h and then diluted with water (20 mL). The aqueous layer was extracted with dichloromethane (3×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was triturated in 50 mL of 1:1 ethyl acetate/hexanes and collected by filtration to obtain 1.7 g of the title compound. MS (ESI+) M/Z 228 [M+H]+.

Provenance & Evidence