Reaktion #2965

ord-840135d79ba844fc945788ee77b22f4f

Reaktionsgleichung

CCN1CC[C@]2(c3cccc(OC)c3)CC(=O)CC[C@H]2C1.Cl
(±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride
CC(=O)C(=NNc1ccccc1)C(=O)Nc1ccccc1
N-phenyl-2-phenylhydrazono-3-oxobutyramide
CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)Nc4ccccc4)c(C)c3C[C@@H]2C1
title compound
Ausbeute 25.6%
CCN1CC[C@@]2(c3cccc(OC)c3)Cc3[nH]c(C(=O)Nc4ccccc4)c(C)c3C[C@@H]2C1
(±)-trans-6-Ethyl-3-methyl-8a-(3-methoxyphenyl)-2-phenylaminocarbonyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline
Ausbeute 25.6%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe residue was purified by flash chromatography (EtOAc/MeOH/conc. NH4OH 90:10:1)

Vorschrift

0.8 g (2.47 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 0.7 g (2.47 mmol) of N-phenyl-2-phenylhydrazono-3-oxobutyramide, 0.24 g (3 mmol) of CH3 COONa, 0.74 g (11.3 mmol) of zinc dust and 2.5 ml of glacial acetic acid were treated as described in example 1. The residue was purified by flash chromatography (EtOAc/MeOH/conc. NH4OH 90:10:1) yielding 0.28 g of the title compound. M.p.=178-180° C.

Quelle

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