Reacción #160770

Ecuación de reacción

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

triethylamine

Boc2O

→

(+/−)-tert-butyl 7-methyl-5-(3-nitropyridin-4-yl)-2-oxo-3a,6,7,7a-tetrahydrobenzo[d]oxazole-3(2H)-carboxylate

Rendimiento 66.0%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe orange reaction
2. 2
   Concentraciónwas then concentrated under vacuo
3. 3
   workup.DISSOLUTIONthe crude was dissolved in ethyl acetate
4. 4
   Secadowater, the organic phase was dried with sodium sulfate
5. 5
   Concentraciónconcentrated under vacuo
6. 6
   workup.DISSOLUTIONThe crude material was dissolved in DCM (0.2M)
7. 7
   Concentraciónconcentrated to dryness
8. 8
   OtroThe crude material was purified via silica gel column chromatography
9. 9
   Lavadoeluting with hexane and ethyl acetate (1:1)

Procedimiento

A solution of (+/−)-2-(tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyl methanesulfonate (1.0 equiv.) in pyridine (0.2M) was heated in the microwave at 110° C. for 10 min. The orange reaction was then concentrated under vacuo, the crude was dissolved in ethyl acetate and water, the organic phase was dried with sodium sulfate and concentrated under vacuo. The crude material was dissolved in DCM (0.2M), triethylamine (1.8 equiv.) was added, followed by Boc2O (1.2 equiv.). The reaction was stirred for 40 min, then concentrated to dryness. The crude material was purified via silica gel column chromatography eluting with hexane and ethyl acetate (1:1) to afford (+/−)-tert-butyl 7-methyl-5-(3-nitropyridin-4-yl)-2-oxo-3a,6,7,7a-tetrahydrobenzo[d]oxazole-3(2H)-carboxylate as a white foam in 66% yield. LC/MS=376.0 (M+H), LC: 3.424 min.

Fuente