Trifluoroacetic acid → HCID 68702636, compound

Participants

Reaction Steps

In a 10 mL round bottom flask was added tert-butyl (S)-2-((ethoxycarbonyl)methoxy)-1-(3-fluorophenyl)ethylcarbamate (69 mg, 0.2 mmol), dichloromethane (1.5 mL), and trifluoroacetic acid (0.5 mL). The solution was stirred at room temperature overnight then concentrated to dryness. The residue was then dissolved in tetrahydrofuran (2 mL) and subsequently treated with DIEA (0.5 mL) and potassium carbonate (excess) and heated 50° C. for 1 h. Upon cooling to room temperature, the reaction solution was diluted with water (3 mL) and extracted with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered and concentrated. Purification on silica gel (40% ethyl acetate/hexanes) gave (S)-5-(3-fluorophenyl)morpholin-3-one (37 mg, 95%) as a colorless oil. HPLC-MS calculated for C10H10FNO2 (M+H+) 196.2, found 196.1.

Provenance & Evidence