Lithium Hydroxide → 1-(2-((tert-butoxycarbonyl)amino)ethyl)cyclopentanecarboxylic acid(WX191663)

Participants

Reaction Conditions

Reaction Steps

To a solution of the 1-[2-[[(1,1-dimethylethoxy)carbonyl]amino]ethyl]cyclopentane carboxylic acid methyl ester (10.6 g, 39.0 mmol) in THF/MeOH (3:1, 40 mL) was added a solution of LiOH (4.20 g, 98.0 mmol) in water (10 mL). The mixture was stirred for 2.5 h at 50° C. and then cooled to room temperature. The reaction mixture was poured into a round bottom flask and concentrated in vacuo. The mixture was diluted with H2O (60 mL) and acidified with 1M HCl. The aqueous phase was extracted with ethyl acetate (3×200 mL) and the combined organic layer was dried over MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography, using hexane-ethyl acetate (3:1), afforded 5.80 g (58%) as a white powder. HR MS (C13H23NO4): Calcd mass, 258.1705. Obs mass, 258.1700 [(M+H).

Provenance & Evidence