반응 #1347413

반응 방정식

triethylamine

Propionyl chloride

3-(5-nitro-pyridin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester

trifluoroacetic acid

→

title compound

수율 85.0%

1-[3-(5-Nitro-pyridin-2-yl)-azetidin-1-yl]-propan-1-one

수율 85.0%

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   농축After concentration
2. 2
   세척washed with saturated aqueous NaHCO3
3. 3
   추출The aqueous phase was extracted with CH2Cl2 (×3)
4. 4
   건조the combined organic layers dried over Na2SO4
5. 5
   기타evaporated
6. 6
   workup.DISSOLUTIONThe raw material was next dissolved in THF (80 ml)
7. 7
   온도the solution cooled to 0° C
8. 8
   기타to reach 20° C.
9. 9
   workup.STIRRINGstirred for a further 12 h
10. 10
    세척washed successively with 1N aqueous HCl, saturated aqueous NaHCO3 and water
11. 11
    건조The organic layer was dried (Na2SO4)
12. 12
    기타evaporated

실험 절차

A solution of 3-(5-nitro-pyridin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (1.22 g, 4.36 mmol) in CH2Cl2 (100 ml) was treated with trifluoroacetic acid (TFA) (15 ml) and then stirred at room temperature for 2 h. After concentration, the raw mixture was digested in CH2Cl2 and washed with saturated aqueous NaHCO3. The aqueous phase was extracted with CH2Cl2 (×3), the combined organic layers dried over Na2SO4 and evaporated. The raw material was next dissolved in THF (80 ml) and the solution cooled to 0° C. Propionyl chloride (460 μl, 5.26 mmol) and triethylamine (735 μl, 5.28 mmol) were next added, the mixture allowed to reach 20° C. and stirred for a further 12 h. It was then diluted with CH2Cl2 and washed successively with 1N aqueous HCl, saturated aqueous NaHCO3 and water. The organic layer was dried (Na2SO4) and evaporated. The residue was chromatographied on silica gel (CH2Cl2:methanol, 49:1) to afford the title compound (880 mg, 85% for two steps) as a brown oil.

출처