Methyl p-toluenesulfonate → (+/-)-benzyl (4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate

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Reaction Steps

Treatment of (±)-1-(4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine (1.11 g, 4.27 mmol) with diisopropylethylamine (1.65 g, 12.8 mmol) followed by benzyl chloroformate (0.87 g, 5.12 mmol) generally according to the procedure described for Intermediate 7 provided 1.5 g (98%) of (±)-benzyl (4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate as a white solid. mp 127-130° C.; Anal. calcd. for C20H20ClNO3: C, 67.13; H, 5.63; N, 3.91. Found: C, 67.03; H, 5.42; N, 3.80. Chiral HPLC separation of (±)-benzyl (4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate (Chiralcel OD, methanol:water 9:1) provided two fractions. Fraction 1 (Rt=12.714 min Chiralcel OD, methanol:water 9:1); Fraction 2 (Rt=16.644 min, Chiralcel OD, methanol:water 9:1).

Provenance & Evidence