Reacción #160769

Ecuación de reacción

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

Rendimiento 65.0%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred for another 2 h
2. 2
   Otrothe reaction
3. 3
   Secadothe organic phase was dried with brine, sodium sulfate
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe crude product was purified via silica gel column chromatography
6. 6
   Lavadoeluting with ethyl acetate and hexanes (1:1)

Procedimiento

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.

Fuente