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

HRID 1292633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1292633
[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]

Komponenten

5

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-07037dcd00224227bbce2b8a4f957a19
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05756863

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