N-Benzyl-5-hydroxycyclohex-3-enecarboxamide → 5-[(Benzylamino)methyl]cyclohex-2-en-1-ol

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (1.50 g, 40.5 mmol) in dry THF (100 ml), cooled in an ice bath, was added drop-wise a solution of N-benzyl-5-hydroxycyclohex-3-enecarboxamide (4.6 g, 20 mmol) in THF (60 ml) over 30 min. The cold bath was removed and the reaction was heated under reflux for 16 h. Then the mixture was cooled in an ice bath and diluted with ether (200 ml), then carefully quenched with water (1.5 ml), 1N sodium hydroxide (4 ml) and water (1.5 ml), successively. After stirring for 45 min, the white suspension was filtered through a glass frit, and the residue was washed with ether. Removal of solvents by rotary evaporation gave the alcohol as a clear, colorless oil (3.8 g, 88%).

Provenance & Evidence