反応 #8858

反応方程式

tert-butyldimethylsilyl chloride

tert-butyl 1-vinyl-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate

imidazole

→

title compound

収率 86.2%

tert-Butyl 1-vinyl-2-(tert-butyldimethylsilyloxy)-8-azaspiro[4.5]decane-8-carboxylate

収率 86.2%

溶媒

ether

sodium bicarbonate

DMF

反応条件

後処理

1. 1
   抽出The mixture was extracted twice with ether
2. 2
   洗浄The combined ether 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 5% ethyl acetate in hexanes

実験手順

To a solution of tert-butyl 1-vinyl-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate (0.462 g, 1.64 mmoL) from Step A in DMF (8 mL) was added imidazole (0.335 mg, 4.92 mmol) and then tert-butyldimethylsilyl chloride (0.370 g, 2.4 mmol). The reaction was stirred at room temperature for 20 h and then diluted with ether and sodium bicarbonate solution. The mixture was extracted twice with ether. The combined ether layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography eluting with 5% ethyl acetate in hexanes to afford the title compound (0.56 g) as a mixture of isomers.

出典