반응 #58349

반응 방정식

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

수율 68.2%

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

수율 68.2%

용매

tert-butanol

ethyl acetate

반응 조건

후처리

1. 1
   온도the reaction mixture is heated to boiling
2. 2
   온도the reaction mixture is cooled
3. 3
   기타The organic phase is dried
4. 4
   농축concentrated
5. 5
   기타the residue is chromatographed on silica gel using
6. 6
   workup.ADDITIONa mixture of petroleum ether/ethyl acetate in the ratio 1/2

실험 절차

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.

출처