Diisopropylamine → Methyl alpha-Cyclopentyl-1-Hydroxycyclohexaneacetate

Participants

Reaction Conditions

Reaction Steps

Diisopropylamine (12.7 g, 0.125) was dissolved in 150 mls of dry THF and cooled to -70° C. under N2. n-Bulb (80 ml of 1.6M solution in hexane, 0.125 moles) was added and the solution stirred for 5 minutes at -70° C. Methyl cyclopentaneacetate (17 g, 0.125 mole) in 50 mls of THF was added at -70° C. over 15 minutes and the reaction was stirred at -70° C. for 15 more minutes. A solution of cyclohexanone (11.3 g, 0.115 moles) in THF (50ml) was then added at -70° C. over 1/2 hour and stirred in the cold for 1 hour. The reaction was warmed to room temperature over 1 hour and quenched with 5 mls of 1N HCl. The solvent was removed on the rotary evaporator and ethyl acetate added. The solution was then washed with saturated NaHCO3 and the layers were separated. The organic layer was dried over Na2SO4. The drying agent was filtered and the filtrate stripped to give a residue which was chromatographed on silica gel using 7% ethyl acetate/hexane to give 27.8 g (92% yield) of the title compound.

Provenance & Evidence