Ammonium Chloride → (2S)-tert-butyl 2-(4-carbamoylphenyl)morpholine-4-carboxylate

Participants

Reaction Steps

To a solution of 4-(2S)-4-(tert-butoxycarbonyl)morpholin-2-yl)benzoic acid (intermediate 16, 22.4 g, 72.9 mmol) in N,N-dimethylformamide (185 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (21.0 g, 109 mmol), 1-hydroxybenzotriazole hydrate (16.8 g, 109 mmol), N,N diisopropylethylamine (37.7 g, 292 mmol) and ammonium chloride (7.80 g, 146 mmol) at room temperature. After stirring for 6 hours the mixture was partitioned between water and ethyl acetate, and the organic layer was washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford (2S)-tert-butyl 2-(4-carbamoylphenyl)morpholine-4-carboxylate (intermediate 17, 20.9 g, 93%).

Provenance & Evidence