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

Temperature

50 °C

In a 100 ml autoclave were charged 3.4 ml of a 0.1M solution of potassium hydroxide (0.34 mmol) in 2-propanol, 4.2 mg (0.02 mmol) of (1S,2S)-diphenylethylenediamine, 1.28 g (10.0 mmol) of 2-methoxycyclohexanone, 8.4 mg (0.005 mmol) of Ru2Cl4 [(S)-BINAP]2NEt3, and 6.5 ml of 2-propanol in a nitrogen atmosphere, and hydrogen was introduced therein to 50 atm. The mixture was stirred at 50° C. for 60 minutes 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 97% d.e. and 92% e.e. by gas chromatography.

1. additionwas introduced
2. temperaturecooled to room temperature
3. customThe solvent was evaporated under reduced pressure
4. distillationthe residue was distilled under reduced pressure

ORD record

ord-07037dcd00224227bbce2b8a4f957a19

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05756863