Tributylstannane → (1S,3R)-2-(3-hydroxy-cyclohexyl)-isoindole-1,3-dione

Participants

Reaction Steps

Tributyltin hydride (1.99 ml, 7.40 mmol) and 2,2′-azobis(isobutyronitrile) (8 mg) were added to a solution of 2-[(1R, 2S, 3S)-2-bromo-3-hydroxycyclohexyl]-1H-isoindole-1,3(2H)-dione (2.0 g, 6.17 mmol) in a mixture of toluene (40 ml) and methanol (4 ml) at room temperature, and the resulting mixture was refluxed for 3 hours. Tributyltin hydride (1.99 ml, 7.40 mmol) and 2,2′-azobis(isobutyronitrile) (8 mg) were further added thereto, and the resulting mixture was refluxed for 1 hour. The reaction solution was concentrated and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=2/1) to obtain cis-2-(3-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione (1.33 g, 88%).

Provenance & Evidence