反応 #157090

反応方程式

Diphenylphosphoryl azide

3-methyl 1-(3-nitropyridin-4-yl)piperidine-3-carboxylic acid

tBuOH

Et3N

→

tert-butyl 3-methyl-1-(3-nitropyridin-4-yl)piperidin-3-ylcarbamate

反応条件

後処理

1. 1
   その他The reaction flask was fitted with an air-cooled
2. 2
   温度reflux condenser
3. 3
   その他bubble vent
4. 4
   workup.ADDITIONThe crude mixture was diluted with EtOAc
5. 5
   洗浄washed with brine
6. 6
   乾燥dried over anhydrous MgSO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo
9. 9
   workup.DISSOLUTIONThe crude residue was dissolved in CH2Cl2
10. 10
    その他purified by flash chromatography (10-20-40% EtOAc in hexanes)

実験手順

Diphenylphosphoryl azide (1.2 eq) was added to a mixture of 3-methyl 1-(3-nitropyridin-4-yl)piperidine-3-carboxylic acid (1 eq) and anhydrous tBuOH (0.3 M), followed shortly by Et3N (2 eq). The reaction flask was fitted with an air-cooled reflux condenser and bubble vent, then heated in an 85° C. oil bath for 3 days. The crude mixture was diluted with EtOAc, washed with brine, then dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude residue was dissolved in CH2Cl2, loaded onto a SiO2 column, and purified by flash chromatography (10-20-40% EtOAc in hexanes) to give tert-butyl 3-methyl-1-(3-nitropyridin-4-yl)piperidin-3-ylcarbamate. LC/MS (m/z): 337.2 (MH+).

出典