N-[tert-Butoxy(hydroxy)methylidene]-3-(trifluoromethyl)phenylalaninato → HCID 66635534, compound

Participants

Reaction Steps

To a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-[3-(trifluoromethyl)phenyl]-propanoic acid (Aldrich) (10.00 g, 30.00 mmol) in tetrahydrofuran (25 mL) with stirring, 1.0 M borane-THF complex in THF (100.0 mL, 100.0 mmol) (newly opened) was added dropwise to keep the internal temperature at 0° C. (release gas, about 15 min). After addition the reaction was stirred at room temperature (rt) for 6 hrs, cooled down with ice-bath, quenched with AcOH:MeOH (1:5, 50 mL), and partitioned between saturated aqueous NaHCO3 and DCM, dried over sodium sulfate, filtered, and evaporated under reduced pressure to give an oil residue, which was purified by combi-flash chromatography to give the desired intermediate. LC-MS found: 320.1 (M+H)+.

Provenance & Evidence