Réaction #2957

ord-3f82d7c91db94bdba2a3ad864f8f9a22

Équation de réaction

CCOC(=O)c1[nH]c2c(c1C)C[C@@H]1CN(CC)CC[C@@]1(c1cccc(OC)c1)C2
(±)-trans-6-ethyl-2-ethoxycarbonyl-3-methyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline
BrB(Br)Br
boron tribromide
→
CCOC(=O)c1[nH]c2c(c1C)C[C@@H]1CN(CC)CC[C@@]1(c1cccc(O)c1)C2
title compound
Rendement 20.9%
CCOC(=O)c1[nH]c2c(c1C)C[C@@H]1CN(CC)CC[C@@]1(c1cccc(O)c1)C2
(±)-trans-6-Ethyl-2-ethoxycarbonyl-8a-(3-hydroxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline
Rendement 20.9%

Réactifs

CCOC(=O)c1[nH]c2c(c1C)C[C@@H]1CN(CC)CC[C@@]1(c1cccc(OC)c1)C2
(±)-trans-6-ethyl-2-ethoxycarbonyl-3-methyl-8a-(3-methoxyphenyl)-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 crude solid was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 80:20:2)

Mode opératoire

0.6 g (1.5 mmol) of (±)-trans-6-ethyl-2-ethoxycarbonyl-3-methyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline were treated with 0.84 ml (9.0 mmol) of boron tribromide as described in example 2. The crude solid was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 80:20:2), yielding 0.12 g of the title compound. M.p.=195°-197° C.

Source

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