Reaktion #2972

ord-3ae2e96f1f8c4014ac444d242c55c3da

Reaktionsgleichung

CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)N(C)C)c(C)c3C[C@@H]2C1
(±)trans-2-dimethylaminocarbonyl-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g] isoquinoline
BrB(Br)Br
boron tribromide
CCOCC.Cl
HCl Et2O
→
CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)N(C)C)c(C)c3C[C@@H]2C1.Cl
title compound
CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)N(C)C)c(C)c3C[C@@H]2C1.Cl
(±)-trans-2-Dimethylaminocarbonyl-6-ethyl-8a-(3-hydroxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline hydrochloride

Edukte

CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)N(C)C)c(C)c3C[C@@H]2C1
(±)trans-2-dimethylaminocarbonyl-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g] isoquinoline
BrB(Br)Br
boron tribromide
CCOCC.Cl
HCl Et2O

Reagenzien

Keine

Lösungsmittel

CO
MeOH

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe solvent was evaporated in vacuo
  2. 2
    Sonstigethe solid crystallized from EtOH

Vorschrift

0.5 g (1.25 mmol) of (±)trans-2-dimethylaminocarbonyl-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g] isoquinoline were treated with 0.725 ml (7.5 mmol) of boron tribromide as described in example 2. The etude product was dissolved in MeOH and the solution brought to acidic pH with HCl/Et2O. The solvent was evaporated in vacuo and the solid crystallized from EtOH, yielding 0.15 g of the title compound. M.p.=305° C. dec.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05731322uspto-grants-1998_03