Benzyl chloroformate → (+/-)-Benzyl(4-phenyl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate

Participants

Reaction Steps

Treatment of (±)-(4-phenyl-2,3-dihydro-1-benzofuran-2-yl)methanamine (0.622 g, 2.38 mmol) with diisopropylethylamine (0.447 g, 3.57 mmol) and benzyl chloroformate (0.462 g, 2.62 mmol) generally according to the procedure described for Intermediate 12 provided 0.601 g (70%) of (±)-benzyl(4-phenyl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate as a white solid. mp 132-134° C.; Anal. calcd. for C23H21NO3: C, 76.86H, 5.89; N, 3.90. Found: C, 75.98H, 5.80; N, 3.72. Chiral HPLC separation of (±)-benzyl(4-phenyl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate (Chiralcel OD, ethanol:water 15:85) provided two fractions. Fraction 1 (Rt=6.651 min Chiralcel OD, ethanol:water 1:3); Fraction 2 (Rt=7.395 min, Chiralcel OD, ethanol:water 1:3).

Provenance & Evidence