2,6-Lutidine → HCID 58530111, compound

Participants

Reaction Conditions

Reaction Steps

A solution of allyl (4S)-4-hydroxy-1-(trifluoroacetyl)-L-prolinate (844 mg, 3.16 mmol) in acetonitrile (16 mL) was cooled to −10° C. and 2,6-lutidine (0.62 mL, 5.32 mmol) was added followed by trifluoromethanesulfonic anhydride (0.85 mL, 5.15 mmol). After addition, the temperature was allowed to warm to 0° C. The reaction mixture was stirred at 0° C. for 1 hour then O-benzylhydroxylamine (1 mL, 8.67 mmol) was added followed by 2,6-lutidine (0.62 mL, 5.32 mmol). The reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was then diluted with ethyl acetate and washed with 5% sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The tan oil residue (2.57 g) was chromatographed on silica gel eluted initially with 95:5 dichloromethane:ethyl acetate and finally with 80:20 dichloromethane:ethyl acetate to afford the title compound as a pale yellow solid.

Provenance & Evidence