Benzyl chloroformate → HCID 53668353, compound

Participants

Reaction Steps

A solution of 4-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-3-fluoronitrobenzene (0.160 g, 0.672 mmol) in 3:1 THF/H2O (4 mL) was treated with acetic acid (0.115 mL) and then 10% palladium/carbon (0.020 g) under a N2 stream. The atmosphere was replaced with H2 (balloon) by repeated evacuation and filling and the mixture stirred at ambient temperature. After 2 h, TLC analysis (6% CH3CN/CHCl3) revealed the reduction to be complete. The reaction mixture was filtered through Celite® and the filtrate immediately placed under an atmosphere of N2 and treated with K2CO3 (0.464 g, 3.36 mmol) followed by benzyl chloroformate (0.117 mL, 0.864 mmol). TLC analysis (6% CH3CN/CHCl3) after 0.5 h revealed the reaction to be complete. The reaction mixture was concentrated under reduced pressure and chromatographed over silica gel (20 g), eluting with a gradient of 1-5% CH3CN/CHCl3. Concentration of appropriate fractions afforded 0.226 g (98%) of the title compound as a white solid with mp 120-121° C. and MS(EI) 342 (M+).

Provenance & Evidence