Reaction #58349

Reaction equation

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

Yield 68.2%

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

Yield 68.2%

Solvents

tert-butanol

ethyl acetate

Conditions

Workup

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

Procedure

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.

Source