Reaktion #670453

Reaktionsgleichung

N-(2-phenylethyl)-4-chlorobutyramide

isopropanol dichloromethane

2,3,5,6-tetrahydro-1H-pyrrolo[2,1-a]isoquinolinium chloride

sodium cyanoborohydride

→

title compound

Ausbeute 70.0%

1,2,3,5,6,10b-Hexahydropyrrolo[2,1-a]isoquinoline

Ausbeute 70.0%

Lösungsmittel

methanol

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthe solvent was concentrated in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in dilute sodium hydroxide
3. 3
   Extraktionwas extracted twice with dichloromethane
4. 4
   TrocknenThe dried (magnesium sulfate) organic phase
5. 5
   Einengenwas concentrated
6. 6
   Sonstigeto give an oil which
7. 7
   workup.DISTILLATIONwas distilled
8. 8
   workup.DISTILLATIONdistilling apparatus, b.p. 100° C. at 0.25 mm

Vorschrift

To a solution of 2,3,5,6-tetrahydro-1H-pyrrolo[2,1-a]isoquinolinium chloride (prepared by the method of S. Akaboshi, T. Kutsuma, and K. Achiwa, J. Pharm. Bull., 1960, 8, 14, from N-(2-phenylethyl)-4-chlorobutyramide (56.4 g, 0.25 mol) and extracted into isopropanol-dichloromethane) in methanol (700 ml) and acetic acid (50 ml) at 0° C. was added portionwise sodium cyanoborohydride (19 g) over 1 h. After stirring overnight, the solvent was concentrated in vacuo. The residue was dissolved in dilute sodium hydroxide and was extracted twice with dichloromethane. The dried (magnesium sulfate) organic phase was concentrated to give an oil which was distilled using a Kugelrohr distilling apparatus, b.p. 100° C. at 0.25 mm, to give the title compound (30.4 g, 70%) as a pale yellow oil.

Quelle