Benzaldehyde → HCID 53724959, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-α-amino-4-(phenylmethoxy)-N-(2,4,6-trifluorophenyl)benzenepropanamide (1.0 g, 2.3 mmol) and benzaldehyde (0.25 g, 2.3 mmol) in toluene was heated under reflux with the azeotropic removal of water (1 hr). The resulting solution was cooled (25° C.), then methanol (30 mL) and an excess of sodium borohydride was added, and the resulting slurry was stirred (2h, 25° C.). To the resulting mixture was added 3% aqueous H2O2 (ca. 10 mL), and the resulting mixture was again stirred (1 hr, 25° C.). The resulting mixture was diluted with ethyl acetate (200 mL), washed with water (2×100 mL), washed with brine (1×100 mL), then dried (MgSO4) and concentrated. The resulting oil was triturated with ether:hexane (1:1) and the resulting precipitate was collected by filtration to yield 0.11 g (9.1%) of the title compound, mp 127°-129° C.

Provenance & Evidence