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

HRID 1292637노트

반응식

HRID 1292637 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3776Isopropanol용매2회

반응 조건

온도
50 °C

실험 절차

In a 100 ml autoclave were charged 1.5 ml of a 0.2M solution of potassium hydroxide (0.30 mmol) in 2-propanol, 4.2 mg (0.02 mmol) of (1S,2S)-diphenylethylenediamine, 1.28 g (10.0 mmol) of 2-methoxycyclohexanone, 10.1 mg (0.01 mmol) of Ir(COD)[(S)-BINAP]BF4, and 8.5 ml of 2-propanol in a nitrogen atmosphere, and hydrogen was introduced therein to 50 atm. The mixture was stirred at 50° C. for 19 hours 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 78% d.e. and 31% e.e. by gas chromatography.

후처리

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

출처 및 근거

ORD 기록
ord-ac8ec51b6c1040b68724244dcfb11275
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05756863

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