1,3-Propanediamine → (1R,2S)-2-methoxycyclohexanol

HRID 1292634Notes

Reaction equation

HRID 1292634 reaction equation
[OH-].[K+].C(N)CCN.[CH3:8][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=[O:16].[H][H]>CC(O)C>[CH3:8][O:9][C@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[OH:16]

Participants

6

Reactant 4

HCID 4281,3-PropanediamineHCID 14797Potassium HydroxideHCID 1109982-MethoxycyclohexanoneHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent3×

Procedure

In a 100 ml autoclave were charged 1.75 ml of a 0.2M solution of potassium hydroxide (0.35 mmol) in 2-propanol, 0.2 ml of a 0.1M solution of 1,3-propanediamine (0.02 mmol) in 2-propanol, 1.28 g (10.0 mmol) of 2-methoxycyclohexanone, 8.4 mg (0.005 mmol) of Ru2Cl4 [(S)-BINAP]2NEt3, and 8 ml of 2-propanol in a nitrogen atmosphere, and hydrogen was introduced therein to 50 atm. The mixture was stirred at room temperature for 1.5 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 93% d.e. and 91% 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-0b4f1140817249edb40c92c31b7ef285
Source dataset
uspto-grants-1998_05
Patent number
US05756863

Reaction notes

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