تفاعل #58349

معادلة التفاعل

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

المردود 68.2%

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

المردود 68.2%

المذيبات

tert-butanol

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture is heated to boiling
2. 2
   درجة الحرارةthe reaction mixture is cooled
3. 3
   أخرىThe organic phase is dried
4. 4
   تركيزconcentrated
5. 5
   أخرىthe residue is chromatographed on silica gel using
6. 6
   workup.ADDITIONa mixture of petroleum ether/ethyl acetate in the ratio 1/2

الإجراء التجريبي

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.

المصدر