反応 #58005

反応方程式

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

溶媒

DCM

反応条件

後処理

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

実験手順

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.

出典