Lithium hydroxide, monohydrate → (S)-2-(Adamantan-1-yloxycarbonylamino)-3,3-dimethyl-butyric acid

Participants

Reaction Steps

To a solution of (S)-2-(Adamantan-1-yloxycarbonylamino)-3,3-dimethyl-butyric acid methyl ester (358 mg, 1.107 mmol) in THF (4 mL) and MeOH (4 mL) was added a pre-made solution of lithium hydroxide monohydrate (93 mg, 2.214 mmol) in water (4.00 mL). The cloudy white solution was stirred at rt for 5 hrs. The volatiles were removed, and the reaction mixture was diluted with dilute citric acid solution and extracted with EtOAc (3×10 mL). The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated to obtain a white solid (291.4 mg, 85%) as product. The crude material was used without further purification.

Provenance & Evidence