Réaction #2974

ord-e576ebaa84304ffda5a1fb2e2ebe1efc

Équation de réaction

CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)N4CCCC4)c(C)c3C[C@@H]2C1
(±)-trans-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-2-pyrrolidinocarbonyl-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)N4CCCC4)c(C)c3C[C@@H]2C1
title compound
Rendement 23.3%
CCN1CC[C@@]2(c3cccc(O)c3)Cc3[nH]c(C(=O)N4CCCC4)c(C)c3C[C@@H]2C1
(±)-trans-6-Ethyl-8a-(3-hydroxyphenyl)-3-methyl-2-pyrrolidinocarbonyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline
Rendement 23.3%

Réactifs

CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)N4CCCC4)c(C)c3C[C@@H]2C1
(±)-trans-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-2-pyrrolidinocarbonyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline
BrB(Br)Br
boron tribromide

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe residue was purified by flash chromatography (EtOAc/MeOH/conc. NH4OH 80:20:0.5)
  2. 2
    AutreThe resulting solid was triturated with Et2O

Mode opératoire

0.63 g (1.37 mmol) of (±)-trans-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-2-pyrrolidinocarbonyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline were treated with 0.77 ml (8.22 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (EtOAc/MeOH/conc. NH4OH 80:20:0.5). The resulting solid was triturated with Et2O, yielding 0.13 g of the title compound. M.p.=224°-226° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05731322uspto-grants-1998_03