4-Fluorobenzylamine → HCID 59512587, compound

Participants

Reaction Steps

To a solution of (S)-5-(4-fluoro-3,5-dimethylbenzyl)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-6-oxohexanal (0.039 g, 0.0917 mmol) and 4-fluorobenzyl amine (0.014 g, 0.110 mmol) in 3 mL of dichloroethane, was added NaBH(OAc)3 (0.027 g, 0.128 mmol). After stirring at room temperature for overnight, the reaction was quenched with 20 mL of saturated NaHCO3 solution and the reaction mixture was extracted with ethyl acetate (20 mL×3). The combined organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The product was isolated by Flash column chromatography (silica gel column) eluting with 0-10% methanol/dichloromethane to give the title compound as light yellow oil (0.030 g, 62% yield). LC-MS: tR=6.9 min; m/z 535 (M+H)+.

Provenance & Evidence