反応 #75617

反応方程式

diethyl ether

trichloroacetyl chloride

sodium bicarbonate

tert-butyl 4-methylene-1-piperidine carboxylate

→

tert-butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

収率 81.1%

溶媒

dimethoxyethane

反応条件

後処理

1. 1
   温度the reaction solution was cooled
2. 2
   その他at 0° C. or less
3. 3
   ろ過The mixture was filtered through Celite
4. 4
   その他evaporated
5. 5
   抽出The resulting residue was extracted with ethyl acetate
6. 6
   洗浄The extract was washed with brine
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   ろ過filtered
9. 9
   その他The filtrate was evaporated

実験手順

49.3 g of tert-butyl 4-methylene-1-piperidine carboxylate was added to a mixture of 157.2 g zinc-copper alloy and 500 ml diethyl ether, and 900 ml solution of 181.8 g trichloroacetyl chloride in dimethoxyethane was added dropwise thereinto over 5.5 hours. After stirred for 30 min, the reaction solution was cooled and saturated aqueous sodium bicarbonate was added thereto at 0° C. or less. The mixture was filtered through Celite and evaporated. The resulting residue was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated, and the resulting residue was subjected to silica gel column chromatography to give 62.5 g of tert-butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylate.

出典