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

Participants

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, 1.1 mg of (0.005 mmol) of (1S,2S)-diphenylethylenediamine, 1.28 g (10.0 mmol) of 2-methoxycyclohexanone, 1.9 mg (0.0001 mmol) of Ru2Cl4 [(S)-DM-BINAP]2NEt3, and 8.5 ml of 2-propanol in a nitrogen atmosphere, and hydrogen was introduced therein to 50 atm. The mixture was stirred at room temperature for 3.5 hours; 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 99% d.e. and 98% e.e. by gas chromatography.

Provenance & Evidence