反応 #353201

反応方程式

triphenylphosphine

cholic acid methyl ester

triphenylphosphine

diphenylphosphorylazide

→

desired product

収率 73.3%

(3β,5β,7α,12α)-3-azido-7,12-dihydroxy-cholan-24-oicacid methyl ester

収率 73.3%

溶媒

THF

THF

反応条件

後処理

1. 1
   その他After a further 24 hours the solvent was evaporated off under reduced pressure
2. 2
   その他the resulting crude was purified by flash chromatography

実験手順

A solution of 2.06 g of cholic acid methyl ester (marketed product) (4.87 mmol), 1.28 g of triphenylphosphine (4.88 mmol) and 1.70 g of diethylazadicarboxylate (0.76 mL, 4.88 mmol) in 50 ml of THF, at room temperature and under inert atmosphere, was added to a solution of 1.4 g of diphenylphosphorylazide (1.1 mL, 5.11 mmol) in 5 ml of THF during 15 minutes. After 24 hours at room temperature, 1 equivalent of diethylazadicarboxylate (0.76 mL, 4.88 mmol) and 1 equivalent of triphenylphosphine (1.28 g, 4.88 mmol) were added. After a further 24 hours the solvent was evaporated off under reduced pressure and the resulting crude was purified by flash chromatography. 1.6 g of the desired product (3.57 mmol) was obtained.

出典