Reaktion #734647

Reaktionsgleichung

Ether

Rochelle salt

(2R*,4aS*,8aS*)-2-Ethyl-2-(3-methoxyphenyl)-4-methyloctahydro-2H-1,4-benzoxazine

di-isobutylaluminium hydride

→

title compound

3-[(2R*,4aS*,8aS*)-2-Ethyl-4-methyloctahydro-2H-1,4-benzoxazin-2yl]phenol

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was then heated
2. 2
   Temperaturto reflux under nitrogen for 51/2 hr
3. 3
   TemperaturThe mixture was cooled in ice to 0°
4. 4
   Sonstigethe phases were separated
5. 5
   workup.ADDITIONThe aqueous phase was then treated with an equal volume of saturated ammonium chloride solution
6. 6
   Extraktionwas extracted with further ether
7. 7
   TrocknenThe combined organic phases were dried (Na2SO4)
8. 8
   Sonstigeevaporated

Vorschrift

(2R*,4aS*,8aS*)-2-Ethyl-2-(3-methoxyphenyl)-4-methyloctahydro-2H-1,4-benzoxazine (0.5 g) in dry toluene (5 cm3) was added under nitrogen to di-isobutylaluminium hydride (20% in toluene, 1.2 M, 15 cm3) at room temperature. The mixture was then heated to reflux under nitrogen for 51/2 hr. The mixture was cooled in ice to 0° and treated cautiously with saturated Rochelle salt solution (75 cm3) and the mixture was stirred for 1 hr. Ether (30 cm3) was added and the phases were separated. The aqueous phase was then treated with an equal volume of saturated ammonium chloride solution and was extracted with further ether. The combined organic phases were dried (Na2SO4) and evaporated, leaving impure title compound base as a cloudy oil which crystallised to a pale yellow mass (0.45 g).

Quelle