반응 #160769

반응 방정식

MsCl

tert-butyl 6-hydroxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate

triethylamine

water

MsCl

→

2-(tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyl methanesulfonate

수율 65.0%

용매

DCM

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for another 2 h
2. 2
   기타the reaction
3. 3
   건조the organic phase was dried with brine, sodium sulfate
4. 4
   농축concentrated
5. 5
   기타The crude product was purified via silica gel column chromatography
6. 6
   세척eluting with ethyl acetate and hexanes (1:1)

실험 절차

To a solution of tert-butyl 6-hydroxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate (1.0 equiv.) in DCM (0.09 M) was added triethylamine (1.5 equiv.) and the reaction was cooled to 0° C. MsCl (1.2 equiv.) was added to the reaction and stirred for 3 h. Another 1.0 equiv. of MsCl was added to the reaction and stirred for another 2 h. Worked up the reaction by adding water, the organic phase was dried with brine, sodium sulfate, and concentrated. The crude product was purified via silica gel column chromatography eluting with ethyl acetate and hexanes (1:1) to afford 2-(tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyl methanesulfonate as a white foam in 65% yield. LC/MS=428.2 (M+H), LC: 3.542 min.

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