反应 #8860

反应方程式

tert-butyl 1-(1-hydroxyprop-1-yl)-2-(tert-butyldimethylsilyloxy)-8-azaspiro[4.5]decane-8-carboxylate

tetrabutylammonium fluoride

→

title compound

收率 99.0%

tert-Butyl 1-(1-hydroxyprop-1-yl)-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate

收率 99.0%

溶剂

ethyl acetate

HCl

THF

THF

反应条件

后处理

1. 1
   萃取extracted twice with ethyl acetate
2. 2
   洗涤The combined organic layers were washed with brine
3. 3
   干燥dried over sodium sulfate
4. 4
   过滤filtered
5. 5
   浓缩concentrated
6. 6
   其他The residue was purified by flash chromatography
7. 7
   洗涤eluting with 50% ethyl acetate in hexanes

实验过程

To a solution of tert-butyl 1-(1-hydroxyprop-1-yl)-2-(tert-butyldimethylsilyloxy)-8-azaspiro[4.5]decane-8-carboxylate (0.248 g, 0.58 mmol) in THF (15 mL) was added 1M tetrabutylammonium fluoride in THF (2.3 mL, 2.3 mmol). The solution was stirred at room temperature for 4 h and was then diluted with ethyl acetate, poured into IN HCl, and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography eluting with 50% ethyl acetate in hexanes to afford the title compound (0.18 g) as a mixture of isomers.

来源