反応 #8860

反応方程式

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

tetrabutylammonium fluoride

→

title compound

収率 99.0%

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

収率 99.0%

溶媒

ethyl acetate

HCl

THF

THF

反応条件

後処理

1. 1
   抽出extracted twice with ethyl acetate
2. 2
   洗浄The combined organic layers were washed with brine
3. 3
   乾燥dried over sodium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他The residue was purified by flash chromatography
7. 7
   洗浄eluting with 50% ethyl acetate in hexanes

実験手順

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.

出典