Reaktion #2966

ord-d7d0772f09424c2a8285b114d4b7d007

Reaktionsgleichung

CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)Nc4ccccc4)c(C)c3C[C@@H]2C1
(±)-trans-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-2-phenylaminocarbonyl-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)Nc4ccccc4)c(C)c3C[C@@H]2C1
title compound
Ausbeute 22.1%
CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)Nc4ccccc4)c(C)c3C[C@@H]2C1
(±)-trans-6-Ethyl-8a-(3-hydroxyphenyl)-3-methyl-2-phenylaminocarbonyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline
Ausbeute 22.1%

Edukte

—
0.35
CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)Nc4ccccc4)c(C)c3C[C@@H]2C1
(±)-trans-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-2-phenylaminocarbonyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline
BrB(Br)Br
boron tribromide

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe residue was purified by flash chromatography (EtOAc/MeOH/conc. NH4OH 80:20:2)

Vorschrift

0.28 g of (±)-trans-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-2-phenylaminocarbonyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline were treated with 0.35 (1.9 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (EtOAc/MeOH/conc. NH4OH 80:20:2) yielding 0.06 g of the title compound. M.p.=271°-272° C.

Quelle

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