반응 #464261

반응 방정식

1-methylpiperazine

2-chloro-1,3-dimethylimidazolinium chloride

dichloromethane

(1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy)cyclopenta[c]-pyrane-4-carboxylic acid

→

(1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy)cyclopenta[c]-pyrane-4-carboxylic acid 4-methylpiperazylamide

수율 50.0%

용매

triethylamine

dichloromethane methanol

반응 조건

후처리

1. 1
   온도was cooled with ice
2. 2
   추출The reaction mixture was then extracted with dichloromethane
3. 3
   세척After washing the organic phase with saturated aqueous sodium bicarbonate and brine, it
4. 4
   건조was dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONAfter distilling off the solvent under reduced pressure
6. 6
   기타the residue was purified by silica gel chromatography

실험 절차

A dichloromethane solution containing 400 mg of (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy)cyclopenta[c]-pyrane-4-carboxylic acid described in Example 1 was cooled with ice followed by addition of 0.20 ml of 1-methylpiperazine, 2 ml of triethylamine and 301 mg of 2-chloro-1,3-dimethylimidazolinium chloride and stirring for 15 hours at room temperature. The reaction mixture was then extracted with dichloromethane. After washing the organic phase with saturated aqueous sodium bicarbonate and brine, it was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a colorless powder from the dichloromethane-methanol eluate in the form of (1S,4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methyl-1-(methylcarbamoyloxy)cyclopenta[c]-pyrane-4-carboxylic acid 4-methylpiperazylamide (264 mg, yield: 50%). The physicochemical properties of this compound are described in Table 5, Compound No. 20.

출처