Potassium Hydroxide → (1R,2S)-2-methoxycyclohexanol

Participants

Reaction Conditions

Reaction Steps

In a 100 ml autoclave were charged 1.5 ml of a 0.2M solution of potassium hydroxide (0.30 mmol) in 2-propanol, 4.2 mg (0.02 mmol) of (1S,2S)-diphenylethylenediamine, 1.28 g (10.0 mmol) of 2-methoxycyclohexanone, 10.1 mg (0.01 mmol) of Ir(COD)[(S)-BINAP]BF4, and 8.5 ml of 2-propanol in a nitrogen atmosphere, and hydrogen was introduced therein to 50 atm. The mixture was stirred at 50° C. for 19 hours and cooled to room temperature. The disappearance of the starting material was confirmed by gas chromatography. The solvent was evaporated under reduced pressure, and the residue was distilled under reduced pressure to obtain (1R,2S)-2-methoxycyclohexanol. The optical purity of the product was found to be 78% d.e. and 31% e.e. by gas chromatography.

Provenance & Evidence