反应 #156307

反应方程式

ammonium chloride

diethylzinc

tert-butyl 4-[(vinyloxy)methyl]piperidine-1-carboxylate

chloroiodomethane

→

tert-butyl 4-[(cyclopropyloxy)methyl]piperidine-1-carboxylate

溶剂

1,2-dichloroethane

1,2-dichloroethane

反应条件

后处理

1. 1
   workup.STIRRINGby stirring for 4 hours
2. 2
   其他from −40° C. to −15° C
3. 3
   萃取followed by extraction with chloroform
4. 4
   洗涤The organic layer was washed with saturated brine
5. 5
   干燥dried over anhydrous magnesium sulfate
6. 6
   浓缩concentrated under reduced pressure
7. 7
   其他The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

实验过程

Under a nitrogen atmosphere, 63 mL of diethylzinc (1.0 M hexane solution) was added to 92 mL of 1,2-dichloroethane at −40° C., and subsequently a solution of 2.5 g of tert-butyl 4-[(vinyloxy)methyl]piperidine-1-carboxylate in 134 mL of 1,2-dichloroethane was added thereto, followed by stirring at −40° C. for 30 minutes. 7.5 mL of chloroiodomethane was added thereto, followed by stirring for 4 hours while elevating the temperature from −40° C. to −15° C. To the reaction mixture was added portionwise a saturated aqueous ammonium chloride solution, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 2.0 g of tert-butyl 4-[(cyclopropyloxy)methyl]piperidine-1-carboxylate.

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