Reaktion #2968

ord-85e68abf33ca4928bc83045893ab7a1b

Reaktionsgleichung

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

Edukte

CCOCC.Cl
HCl Et2O
—
crude product
CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)N(C(C)C)C(C)C)c(C)c3C[C@@H]2C1
(±)-trans-2-diisopropylaminocarbonyl-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

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 acetone

Vorschrift

1.0 g (2.2 mmol) of (±)-trans-2-diisopropylaminocarbonyl-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 1.15 ml (12.0 mmol) of boron tribromide as described in example 2. The crude 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 acetone, yielding 0.5 g of the title compound. M.p.=263°-265° C.

Quelle

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