반응 #464265

반응 방정식

triethylamine

methylisocyanate

acetonitrile

(4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-1-hydroxy-7-methylcyclopenta[c]pyrane-4-carboxylic acid methylester

→

(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 methylester

수율 61.7%

용매

hexane ethyl acetate

반응 조건

후처리

1. 1
   온도was cooled with ice
2. 2
   추출The reaction mixture was then extracted with ethyl acetate
3. 3
   세척After washing the organic phase with 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

An acetonitrile solution containing 790 mg of a known (4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-1-hydroxy-7-methylcyclopenta[c]pyrane-4-carboxylic acid methylester was cooled with ice followed by addition of 0.54 ml of triethylamine and 0.23 ml of methylisocyanate and stirring for 15 hours at room temperature. The reaction mixture was then extracted with ethyl acetate. After washing the organic phase with 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 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 methylester (610 mg, yield: 61.7%). The physicochemical properties of this compound are described in Table 1, Compound No. 3.

출처