Réaction #58347

Équation de réaction

(±)-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

Rendement 87.8%

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

Rendement 87.8%

Solvants

1,2-dimethoxyethane

Conditions de réaction

Traitement

1. 1
   ConcentrationThe reaction mixture is concentrated
2. 2
   workup.DISSOLUTIONthe residue redissolved in ethyl acetate
3. 3
   Extractionextracted with water
4. 4
   AutreThe organic layer is dried
5. 5
   Concentrationconcentrated
6. 6
   Autrethe residue is chromatographed on silica gel using
7. 7
   workup.ADDITIONa mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 6/3/1

Mode opératoire

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.

Source