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

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Reaction Steps

Treatment of (±)-1-(5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine (0.51 g, 1.96 mmol) with diisopropylethylamine (0.76 g, 5.88 mmol) followed by benzyl chloroformate (0.50 g, 2.94 mmol) generally according to the procedure described for Intermediate 7 provided 0.58 g (84%) of (±)-benzyl (5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate as a white solid. mp 118-121° C.; Anal. calcd. for C20H20ClNO3: C, 67.13; H, 5.63; N, 3.91. Found: C, 66.95; H, 5.93; N, 3.82. Chiral HPLC separation of (±)-benzyl (5-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate (Chiralpak AD, hexane:isopropanol 9:1) provided two fractions. Fraction 1 (Rt=11.191 min, Chiralpak AD, hexane:isopropanol 9:1); Fraction 2 (Rt=12.735 min, Chiralpak AD, hexane:isopropanol 9:1).

Provenance & Evidence