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

HRID 1292637ノート

反応式

HRID 1292637 の反応式
[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]

参加物

5

反応物 3

HCID 14797Potassium HydroxideHCID 1109982-MethoxycyclohexanoneHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒2 回

反応条件

温度
50 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-ac8ec51b6c1040b68724244dcfb11275
出典データセット
uspto-grants-1998_05
特許番号
US05756863

反応ノート

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