Benzyl chloroformate → HCID 131727105, compound

Participants

Reaction Steps

Treatment of (±)-[7-(2-isopropylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methylamine (1.69 g, 5.56 mmol) with diisopropylethylamine (1.08 g, 8.34 mmol) and benzyl chloroformate (1.04 g, 6.12 mmol) generally according to the procedure described for Intermediate 12 gave 1.92 (89%) of (±)-benzyl[7-(2-isopropylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate as a yellow oil. Rf=0.66 (silica, ethyl acetate:hexanes 1:4); Anal. calcd. for C26H27NO3: C, 77.78; H, 6.78; N, 3.49. Found: C, 77.5; H, 6.7; N, 3.33. Chiral HPLC separation of (±)-[7-(2-isopropylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate (Chiralcel OD, hexane:isopropanol 9:1) provided two fractions. Fraction 1 (Rt=8.131 min, Chiralcel OD, hexane:isopropanol 9:1); Fraction 2 (Rt=11.048 min, Chiralcel OD, hexane:isopropanol 9:1).

Provenance & Evidence