Reaktion #2964

ord-2895d0d365944737af7826beeea98209

Reaktionsgleichung

COc1cccc([C@@]23CCN(C)C[C@H]2Cc2c([nH]c(C(=O)NCc4ccccc4)c2C)C3)c1
(±)-trans-2-benzylaminocarbonyl-3,6-dimethyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline
BrB(Br)Br
boron tribromide
CCOCC.Cl
HCl Et2O
→
Cc1c(C(=O)NCc2ccccc2)[nH]c2c1C[C@@H]1CN(C)CC[C@@]1(c1cccc(O)c1)C2.Cl
title compound
Cc1c(C(=O)NCc2ccccc2)[nH]c2c1C[C@@H]1CN(C)CC[C@@]1(c1cccc(O)c1)C2.Cl
(±)-trans-2-Benzylaminocarbonyl-3,6-dimethyl-8a-(3-hydroxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline hydrochloride

Edukte

COc1cccc([C@@]23CCN(C)C[C@H]2Cc2c([nH]c(C(=O)NCc4ccccc4)c2C)C3)c1
(±)-trans-2-benzylaminocarbonyl-3,6-dimethyl-8a-(3-methoxyphenyl)-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 crystallised from a mixture of acetone/MeOH=1:1

Vorschrift

0.38 g of (±)-trans-2-benzylaminocarbonyl-3,6-dimethyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline were treated with 0.55 ml (5.7 mmol) of boron tribromide as described in example 2. The residue was dissolved in MeOH and the solution brought to acidic pH with HCl/Et2O. The solvent was evaporated in vacuo and the solid crystallised from a mixture of acetone/MeOH=1:1, yielding 0.15 g of the title compound. M.p.=297°-299° C. C27H31N3 O2.HCl I.R. (KBr): 3290, 2910, 1650, 1540, 1320cm-1

Quelle

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