Réaction #156307

Équation de réaction

ammonium chloride

diethylzinc

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

chloroiodomethane

→

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

Solvants

1,2-dichloroethane

1,2-dichloroethane

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source