Benzyl succinimido carbonate → 1,3,4,9-Tetrahydro-beta-carboline-2-carboxylic acid benzyl ester

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Reaction Steps

A solution of N-(benzyloxycarbonyloxy)succinimide (9.61 g, 38.6 mmol) in anhydrous tetrahydrofuran (30 ml) was added to a suspension of 2,3,4,9-tetrahydro-1H-β-carboline (4.43 g, 25.7 mmol) and 4-N,N-dimethylaminopyridine (266 mg) in anhydrous tetrahydrofuran (30 ml), while cooling with ice. The suspension was stirred at room temperature for 16 h and the tetrahydrofuran was then removed i. vac. The residue was dissolved in ethyl acetate (20 ml) and the solution was washed with water (2×20 ml). The organic phase was dried with sodium sulfate and concentrated i. vac. The crude product (11.0 g) was purified by flash chromatography with cyclohexane/ethyl acetate (4:1).

Provenance & Evidence