Réaction #2959

ord-c4dcc751dbde49eaa01591fb6c337bfc

Équation de réaction

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

Réactifs

CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)OCC(C)C)c(C)c3C[C@@H]2C1.Cl
(±)-trans-2-(i-butoxycarbonyl)-6-ethyl-3-methyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline hydrochloride
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 (AcOEt/MeOH/conc. NH4OH 75:25:2.5)
  2. 2
    Autrecrystallised from AcOEt yielding 0.1 g of the title compound

Mode opératoire

0.56 g of (±)-trans-2-(i-butoxycarbonyl)-6-ethyl-3-methyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline hydrochloride were treated with 0.68 ml (7.26 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 75:25:2.5) and then crystallised from AcOEt yielding 0.1 g of the title compound. M.p.=196°-198° C.

Source

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