Benzyl chloroformate → HCID 86599137, compound

Participants

Reaction Steps

Treatment of (±)-1-[7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine (0.947 g, 3.73 mmol) with diisopropylethylamine (0.725 g, 5.60 mmol) followed by benzyl chloroformate (0.765 g, 4.48 mmol) generally according to the procedure described for Intermediate 12 provided 1,26 g (87%) of (±)-benzyl {[7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate as a colorless oil. Anal. calcd. for C25H25NO3: C, 77.49; H, 6.5; N, 3.61. Found: C, 77.42; H, 6.57; N, 3.62. Chiral HPLC separation of (±)-benzyl {[7-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate (Chiralcel OJ, methanol:carbon dioxide 4:6) provided two fractions. Fraction 1 (Rt=3.12 min, Chiralcel OJ, methanol:carbon dioxide 4:6); Fraction 2 (Rt=4.28 min, Chiralcel OJ methanol:carbon dioxide 4:6).

Provenance & Evidence