반응 #160770

반응 방정식

(+/−)-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

수율 66.0%

용매

pyridine

반응 조건

후처리

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

실험 절차

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.

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