Reaktion #156307

Reaktionsgleichung

ammonium chloride

diethylzinc

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

chloroiodomethane

→

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

Lösungsmittel

1,2-dichloroethane

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle