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

HRID 1292635Notes

Reaction equation

HRID 1292635 reaction equation
[OH-].[K+].[CH3:3][O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11].[H][H]>CC(O)C>[CH3:3][O:4][C@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[OH:11]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 1109982-MethoxycyclohexanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 6951180(1R,2S)-2-methoxycyclohexanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

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.

Workup

  1. additionwas introduced
  2. customThe solvent was evaporated under reduced pressure
  3. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-c46db035a57941628f25c83c9f572bfb
Source dataset
uspto-grants-1998_05
Patent number
US05756863

Reaction notes

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