Reacción #156307

Ecuación de reacción

ammonium chloride

diethylzinc

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

chloroiodomethane

→

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

Disolventes

1,2-dichloroethane

1,2-dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGby stirring for 4 hours
2. 2
   Otrofrom −40° C. to −15° C
3. 3
   Extracciónfollowed by extraction with chloroform
4. 4
   LavadoThe organic layer was washed with saturated brine
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Procedimiento

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.

Fuente