Réaction #2958

ord-9a47955b82844c658fba77886c3a3881

Équation de réaction

CCCN(CCC)C(=O)n1cc(C)c2c1C[C@]1(c3cccc(OC)c3)CCN(CC)C[C@H]1C2.Cl
(±)-trans-dipropylaminocarbonyl-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
→
CCCN(CCC)C(=O)n1cc(C)c2c1C[C@]1(c3cccc(O)c3)CCN(CC)C[C@H]1C2
(±)-trans-Dipropylaminocarbonyl-6-ethyl-8a-(3-hydroxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline

Réactifs

CCCN(CCC)C(=O)n1cc(C)c2c1C[C@]1(c3cccc(OC)c3)CCN(CC)C[C@H]1C2.Cl
(±)-trans-dipropylaminocarbonyl-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
    AutreThe crude product was crystallised from acetone yielding 0.075 g of the title compound

Mode opératoire

0.56 g (1.15 mmol) of (±)-trans-dipropylaminocarbonyl-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 0.65 ml (7 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 75:25:2.5). The crude product was crystallised from acetone yielding 0.075 g of the title compound. M.p.=151°-153° C.

Source

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