Menthol → HCID 66939725, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(3-Fluoro-benzylidene)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (2.68 g, 8.35 mmol), 1R,2S,5R(−) menthol (1.31 g, 8.35 mmol) was added followed by dimethylaminopyridine (1.02 g, 8.35 mmol). The mixture was cooled to 0° C. and dicyclohexylcarbodiimide (1.89 g, 9.19 mmol) in dichloromethane (10 ml) was added in one portion. The mixture was warmed to room temperature stirred for 18 h. The mixture was filtered and the filtrate was washed with 1N hydrochloric acid (30 ml), sat. sodium hydrogen carbonate (30 ml) and water (30 ml). The organics were dried over magnesium sulphate and the solvent was removed by evaporation under reduced pressure. Purification by flashmaster column chromatography eluting with heptane:ethyl acetate (12:1) yielded the title compound (1.20 g, 31%) as a colourless oil.

Provenance & Evidence