Benzyl chloroformate → HCID 19753252, compound

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Reaction Steps

Sodium bicarbonate (7.20 g) is added to a solution of 5-aminoindan (XVA, 5.71 g) in acetone (60 ml) and water (30 ml) 0°, followed by the dropwise addition of benzylchloroformate (6.8 ml, 8.07 g) over 5 min. The mixture is stirred at 0° for about 1 hr, then at 20°-25° overnight. The mixture is poured into aqueous sodium hydrogen sulfate (10%, 200 ml), and ethyl acetate (300 ml). The organic extract is washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated under reduced pressure to give an oil. The oil is purified by column chromatography on 60-200 μsilica gel, eluting with ethyl acetate/hexane (10/90). The appropriate fractions are pooled and concentrated to give the title compound, mp 56°-59°; NMR (CDCl3, 300 MHz) 7.40-7.03, 7.11, 7.05, 6.65, 5.18, 2.85 and 2.05 δ; IR (mineral oil mull) 3275, 2925, 1693.5, 1544 and 1236 cm-1 ; MS (m/e) 267, 223, 222 and 91.

Provenance & Evidence