Benzyl chloroformate → HCID 91385942, compound

Participants

Reaction Steps

Treatment of (±)-[7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine (3.55 g, 12.9 mmol) with diisopropylethylamine (2.5 g, 19.4 mmol) and benzyl chloroformate (2.42 g, 14.2 mmol) generally according to the procedure described for Intermediate 12 provided 4.1 g (85%) of (±)-benzyl[7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate as a clear oil Rf=0.64 (silica, ethyl acetate:hexanes 1:4); Anal. calcd. for C24H23F4NO3: C, 77.19; H, 6.21; N, 3.75. Found: C, 76.95; H, 6.18; N, 3.53. Chiral HPLC separation of (±)-benzyl[7-(2-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate (Chiralcel OD, isopropanol:hexane 1:4) provided two fractions. Fraction 1 (Rt=7.285 min, isopropanol:hexane 1:4); Fraction 2 (Rt=9.361 min, Chiralcel OD, isopropanol:hexane 1:4).

Provenance & Evidence