Benzyl chloroformate → HCID 86601825, compound

Participants

Reaction Steps

Treatment of (±)-1-(7-thien-3-yl-2,3-dihydro-1-benzofuran-2-yl)methanamine (0.56 g, 2.09 mmol) with diisopropylethylamine (0.406 g, 3.14 mmol) and benzyl chloroformate (0.393 g, 2.30 mmol) generally according to the procedure described for Intermediate 12 provided 0.54 g (71%) of (±)-benzyl(7-thien-3-yl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate as a colorless oil. Rf=0.49 (silica, ethyl acetate:hexanes 2:8); Anal. calcd. for C21H19NO3S.0.3H2O: C, 68.01; H, 5.33; N, 3.78. Found: C, 67.88; H, 5.18; N, 3.72. Chiral HPLC separation of (±)-benzyl(7-thien-3-yl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate (Chiralcel AD, water:methanol 1:9) provided two fractions. Fraction 1 (Rt=13.00 min, (Chiralcel AD, water:methanol 1:9); Fraction 2 (Rt=14.1 min, (Chiralcel AD, water:methanol 1:9).

Provenance & Evidence