反応 #58347

反応方程式

(±)-3,4-bis-cyclopropylmethoxy-N-[(1RS,2RS)-2-(3,4-dimethoxyphenyl)-5-oxo-cyclohexyl]benzamide

compound C1

(±)-3,4-bis-cyclopropylmethoxy-N-[(1RS,2RS)-2-(3,4-dimethoxyphenyl)-5-oxo-cyclohexyl]benzamide

methanol

sodium borohydride

→

title compound

収率 87.8%

(±)-3,4-Bis-cyclopropylmethoxy-N-[(1RS,2RS,5SR)-2-(3,4-dimethoxyphenyl)-5-hydroxycyclohexyl]benzamide

収率 87.8%

溶媒

1,2-dimethoxyethane

反応条件

後処理

1. 1
   濃縮The reaction mixture is concentrated
2. 2
   workup.DISSOLUTIONthe residue redissolved in ethyl acetate
3. 3
   抽出extracted with water
4. 4
   その他The organic layer is dried
5. 5
   濃縮concentrated
6. 6
   その他the residue is chromatographed on silica gel using
7. 7
   workup.ADDITIONa mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 6/3/1

実験手順

7.2 g of (±)-3,4-bis-cyclopropylmethoxy-N-[(1RS,2RS)-2-(3,4-dimethoxyphenyl)-5-oxo-cyclohexyl]benzamide (compound C1) are dissolved in 550 ml of 1,2-dimethoxyethane and 34 ml of methanol and treated portionwise with 600 mg of sodium borohydride at room temperature. The reaction mixture is concentrated, the residue redissolved in ethyl acetate and extracted with water. The organic layer is dried using sodium sulfate, concentrated and the residue is chromatographed on silica gel using a mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 6/3/1. 6.35 g of the title compound are obtained.

出典