Reaktion #58350

Reaktionsgleichung

(±)-cis-3,4-bis-cyclopropylmethoxy-N-[6-(3,4-dimethoxyphenyl)cyclohex-3-enyl]benzamide

compound F1

(±)-cis-3,4-bis-cyclopropylmethoxy-N-[6-(3,4-dimethoxyphenyl)cyclohex-3-enyl]benzamide

m-chloroperbenzoic acid

→

title compound

Ausbeute 68.0%

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

Ausbeute 68.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe reaction mixture is extracted with sodium hydrogencarbonate solution and water
2. 2
   Sonstigethe organic phase is dried
3. 3
   Einengenconcentrated
4. 4
   SonstigeThe residue is chromatographed on silica gel using a
5. 5
   workup.ADDITIONa mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 4/4/1

Vorschrift

37.7 g of (±)-cis-3,4-bis-cyclopropylmethoxy-N-[6-(3,4-dimethoxyphenyl)cyclohex-3-enyl]benzamide (compound F1) are dissolved in 470 ml of dichloromethane and treated with 27.4 g of m-chloroperbenzoic acid. After stirring over night at room temperature, the reaction mixture is extracted with sodium hydrogencarbonate solution and water, the organic phase is dried using sodium sulfate and concentrated. The residue is chromatographed on silica gel using a a mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 4/4/1. 26.5 g of the title compound are obtained.

Quelle