Benzyl chloroformate → 4-Oxo-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid benzyl ester

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Reaction Steps

Benzyloxycarbonyl chloride (5.14 ml, 36.0 mmol) was added dropwise to a solution of 7-benzyl-2-oxo-7-azabicyclo [3.3.0]octane (5.20 g, 24.2 mmol) in dichloromethane (50 ml) under cooling with ice, followed by stirring at room temperature for 24 hours. The mixture was again cooled with ice, and benzyloxycarbonyl chloride (5.14 ml, 36.0 mmol) was added thereto dropwise. After removing the solvent by evaporation, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give 4.52 g (17.4 mmol, 72%) of the title compound as acolorless oily substance. 1H-NMR (400 MHz, CDCl3) δ: 1.80-1.90 (1H, m), 2.12-2.22 (1H, m), 2.35-2.39 (2H, m), 2.76 (1H, dt, J=3.5, 8.5 Hz), 3.01-3.11 (1H, m), 3.16-3.26 (1H, m), 3.61-3.66 (1H, m), 3.69-3.78 (1H, m), 5.11-5.12 (2H, m), 7.29-7.38 (5H, m)

Provenance & Evidence