(+/-)-trans-2-Ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride → (+/-)-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

HRID 2869Notes

Reaction equation

HRID 2869 reaction equation
Cl.[CH2:2]([N:4]1[CH2:13][CH2:12][C@@:11]2([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[C@@H:6]([CH2:7][CH2:8][C:9](=O)[CH2:10]2)[CH2:5]1)[CH3:3].[C:23]1([NH:29][C:30](=[O:43])[C:31](=[N:35]NC2C=CC=CC=2)[C:32](=O)[CH3:33])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>[Zn].C(O)(=O)C>[CH2:2]([N:4]1[CH2:13][CH2:12][C@:11]2([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[C@H:6]([CH2:7][C:8]3[C:32]([CH3:33])=[C:31]([C:30]([NH:29][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:43])[NH:35][C:9]=3[CH2:10]2)[CH2:5]1)[CH3:3]

Participants

5

Reactant 2

HCID 86752325(+/-)-trans-2-Ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochlorideHCID 178418293HCID 178418293, compound

Product 1

HCID 22883679(+/-)-trans-6-Ethyl-3-methyl-8a-(3-methoxyphenyl)-2-phenylaminocarbonyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinolineYield 25.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-840135d79ba844fc945788ee77b22f4f
Source dataset
uspto-grants-1998_03
Patent number
US05731322

Reaction notes

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