Reaktion #311459

Reaktionsgleichung

hydrogen chloride

sodium bis(2-methoxyethoxy)aluminum hydride

N-methyl-1-phenyl-1,2-cyclopropanedicarboxamide

hydride

sodium hydroxide

→

Racemic 3-Methyl-1-phenyl-3-azabicyclo[3.1.0]-hexane hydrochloride

Lösungsmittel

benzene

water

ether

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is heated
2. 2
   Temperaturat reflux under nitrogen for 90 minutes
3. 3
   SonstigeThe benzene phase is separated
4. 4
   Extraktionthe aqueous phase is extracted with chloroform
5. 5
   TrocknenThe combined organic phases are dried over magnesium sulfate
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   Sonstigegiving a liquid
8. 8
   Sonstigeis recrystallized from isopropyl alcohol-hexane giving white crystals, m.p. 158°-160° C.

Vorschrift

To a stirred solution of 30 ml of sodium bis(2-methoxyethoxy)aluminum hydride (70% benzene solution) is added dropwise a solution of 5.5 g of N-methyl-1-phenyl-1,2-cyclopropanedicarboxamide (U.S. Pat. No. 3,166,571-Ex. 1) in 400 ml of benzene over a one hour period at room temperature under nitrogen. The mixture is heated at reflux under nitrogen for 90 minutes. The excess hydride reagent is decomposed by the cautious addition of 25 ml of 10 N sodium hydroxide and then diluted to 200 ml with water. The benzene phase is separated and the aqueous phase is extracted with chloroform. The combined organic phases are dried over magnesium sulfate and concentrated under reduced pressure giving a liquid. The liquid is dissolved in ethanol and acidified with 15 ml of 2.3 N ethanolic hydrogen chloride. The addition of ether causes the formation of a solid which is recrystallized from isopropyl alcohol-hexane giving white crystals, m.p. 158°-160° C.

Quelle