反応 #58349

反応方程式

methanol

(±)-3,4-bis-cyclopropylmethoxy-N-[(3RS,4RS)-4-(3,4-dimethoxyphenyl)-7-oxabicyclo[4.1.0]-hept-3-yl]benzamide

compound E1

(±)-3,4-bis-cyclopropylmethoxy-N-[(3RS,4RS)-4-(3,4-dimethoxyphenyl)-7-oxabicyclo[4.1.0]-hept-3-yl]benzamide

water

sodium borohydride

→

title compound

収率 68.2%

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

収率 68.2%

溶媒

tert-butanol

ethyl acetate

反応条件

後処理

1. 1
   温度the reaction mixture is heated to boiling
2. 2
   温度the reaction mixture is cooled
3. 3
   その他The organic phase is dried
4. 4
   濃縮concentrated
5. 5
   その他the residue is chromatographed on silica gel using
6. 6
   workup.ADDITIONa mixture of petroleum ether/ethyl acetate in the ratio 1/2

実験手順

16.5 g of (±)-3,4-bis-cyclopropylmethoxy-N-[(3RS,4RS)-4-(3,4-dimethoxyphenyl)-7-oxabicyclo[4.1.0]-hept-3-yl]benzamide (compound E1) are dissolved in 500 ml of tert-butanol, 5.0 g of sodium borohydride are added and the reaction mixture is heated to boiling. After slow addition of 70 ml of methanol, the reaction mixture is cooled and treated with 200 ml of water and 150 ml of ethyl acetate. The organic phase is dried using sodium sulfate, concentrated and the residue is chromatographed on silica gel using a mixture of petroleum ether/ethyl acetate in the ratio 1/2. 11.3 g of the title compound are obtained.

出典