反应 #58005

反应方程式

alcohol

tert-butyl 4-{2-[(1R)-1-hydroxypropyl]-4,5-dimethylphenyl)-3,6-dihydropyridine-1(2H)-carboxylate

triphenylphosphine

imidazole

→

azide

tert-butyl 4-{2-[(1S)-1-hydroxypropyl]-4,5-dimethylphenyl}-3,6-dihydropyridine-1(2H)-carboxylate

溶剂

DCM

反应条件

后处理

1. 1
   其他2Py (prepared
2. 2
   workup.ADDITIONAfter the addition
3. 3
   过滤The reaction mixture was filtered through a short column of silica gel
4. 4
   洗涤eluted with the appropriate volume of DCM
5. 5
   其他to remove excess salts and polar byproducts
6. 6
   浓缩The filtrate was concentrated in vacuo
7. 7
   其他the crude residue purified by flash chromatography on silica gel (gradient elution; 0%-20% EtOAc/hexanes as eluent)

实验过程

Diisopropylazidocarboxylate (2.96 mL, 15.1 mmol) was added dropwise to a stirred mixture of alcohol 109 (1.3 g, 3.76 mmol), Zn(N3)2.2Py (prepared according to the method described by Viaud, M-C; Rollin, P. in Synthesis, 1990,130), triphenylphosphine (3.95 g, 15.1 mmol) and imidazole (1.03 g, 15.1 mmol) in DCM (100 mL) at approximately 0° C. After the addition, the resulting mixture was allowed to warm to ambient temperature and stirred vigorously for 18 h. The reaction mixture was filtered through a short column of silica gel eluted with the appropriate volume of DCM to remove excess salts and polar byproducts. The filtrate was concentrated in vacuo and the crude residue purified by flash chromatography on silica gel (gradient elution; 0%-20% EtOAc/hexanes as eluent) to afford azide 110 as a colorless oil.

来源