Benzyl chloroformate → HCID 86599087, compound

Participants

Reaction Steps

Treatment of (±)-1-{7-[2-(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl}methanamine (0.813 g, 2.46 mmol) with diisopropylethylamine (0.478 g, 3.69 mmol) and benzyl chloroformate (0.462 g, 2.71 mmol) generally according to the procedure described for Intermediate 12 gave 0.99 g (94%) of (±)-benzyl {7-[2-(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl}methylcarbamate as a pale yellow oil Rf=0.60 (silica, ethyl acetate:hexanes 2:8); Anal. calcd. for C24H20F3NO3: C, 67.44; H, 4.71; N, 3.15. Found: C, 67.43H, 4.76; N, 3.15. Chiral HPLC separation of (±)-benzyl[7-(2-(trifluoromethyl))-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate (Chiralcel OJ, isopropanol:carbon dioxide 3:17) provided two fractions. Fraction 1 (Rt=5.252 min, Chiralcel OJ, isopropanol:carbon dioxide 3:17); Fraction 2 (Rt=6.280 min, Chiralcel OJ, isopropanol:carbon dioxide 3:17).

Provenance & Evidence