Reaktion #1667648

Reaktionsgleichung

1,2,3,4,8,9-hexahydro-3-methylpyrido[4',3':2,3]indolo[1,7-ab][1]benzazepine

boron hydride

→

trans-1,2,3,4,4a,8,9,14a-Octahydro-3-methylpyrido[4',3':2,3]indolo[1,7-ab][1]benzazepine

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturthe mixture was refluxed under nitrogen for five hours
3. 3
   Temperaturcooled in ice
4. 4
   Sonstigequenched with 20 ml
5. 5
   workup.DISTILLATIONThe mixture was distilled
6. 6
   workup.ADDITIONreplaced by addition of dioxane
7. 7
   Temperaturcooled to 70°C.
8. 8
   Sonstigeevaporated in vacuum
9. 9
   workup.ADDITIONThe semisolid residue was treated with water and chloroform
10. 10
    Sonstigeto yield 1.50 g
11. 11
    SonstigeThe mother liquors yielded an additional amount of material, m.p. 129.5°-130.5°C
12. 12
    SonstigeCrystallization from ether
13. 13
    Temperaturraised the melting point to 132°-134°C.

Vorschrift

A solution of 4.76 g. of 1,2,3,4,8,9-hexahydro-3-methylpyrido[4',3':2,3]indolo[1,7-ab][1]benzazepine (which can be made according to the teachings of U.S. Pat. No. 3,457,271, Column 4, lines 27-54) in 50 ml. of tetrahydrofuran was added dropwise to a stirred 1N-solution of boron hydride in tetrahydrofuran (42 ml.) under a nitrogen blanket. After the addition was complete, the mixture was refluxed under nitrogen for five hours, then cooled in ice and quenched with 20 ml. of 6N hydrochloric acid. The mixture was distilled, the removed liquid being from time to time replaced by addition of dioxane. The mixture was again refluxed at 91°C. for one hour with additional 6N hydrochloric acid, then cooled to 70°C., made basic with sodium hydroxide, and evaporated in vacuum. The semisolid residue was treated with water and chloroform, and the chloroform layer was further worked up to yield 1.50 g. of a solid product, m.p. 128°-131°C. The mother liquors yielded an additional amount of material, m.p. 129.5°-130.5°C. Crystallization from ether raised the melting point to 132°-134°C.; UV spectrum: λmaxCH3OH 279.5 mμ (logε 4.13).

Quelle