반응 #464255

반응 방정식

(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

potassium carbonate

diethyl sulfate

acetonitrile

→

(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 ethylester

수율 88.0%

용매

hexane ethyl acetate

반응 조건

후처리

1. 1
   온도by heating
2. 2
   추출The reaction mixture was then extracted with ethyl acetate
3. 3
   세척After washing the organic phase with dilute hydrochloric acid, 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

130 mg of potassium carbonate and 121 μl of diethyl sulfate were added to an acetonitrile solution containing 210 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 followed by heating and stirring for 1 hour at 70° C. The reaction mixture was then extracted with ethyl acetate. After washing the organic phase with dilute hydrochloric acid, 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 oil from the hexane-ethyl acetate 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 ethylester (204 mg, yield: 88%). The physicochemical properties of this compound are described in Table 1, Compound No. 4.

출처