(+/-)-trans-2-Ethyl-4a-(3-methoxyphenyl)-7-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride → (+/-)-trans-2-diethylaminocarbonyl-3,7-dimethyl-4a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[3,2-g]isoquinoline

HRID 2865Notes

Reaction equation

HRID 2865 reaction equation
Cl.C([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](=O)[CH2:9][CH2:10]2)[CH2:5]1)C.[CH2:23]([N:25]([CH2:40][CH3:41])[C:26](=[O:39])[C:27](=[N:31]NC1C=CC=CC=1)[C:28](=O)[CH3:29])[CH3:24].[CH3:42]C(O[Na])=O>[Zn].C(O)(=O)C>[CH2:40]([N:25]([CH2:23][CH3:24])[C:26]([C:27]1[NH:31][C:8]2[CH2:9][C@@H:12]3[C@:11]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=4)([CH2:10][CH2:42][N:4]([CH3:5])[CH2:13]3)[CH2:6][C:7]=2[C:28]=1[CH3:29])=[O:39])[CH3:41]

Participants

6

Reactant 3

HCID 86752329(+/-)-trans-2-Ethyl-4a-(3-methoxyphenyl)-7-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochlorideHCID 178418240HCID 178418240, compoundHCID 178418247HCID 178418247, compound

Product 1

HCID 70106403(+/-)-trans-2-diethylaminocarbonyl-3,7-dimethyl-4a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[3,2-g]isoquinolineYield 16.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

0.9 g (2.9 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-7-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride (J. Med. Chem., 35, 48, 1992), 0.9 g (3.5 mmol) of N,N-diethyl-2-phenylhydrazono-3-oxobutyramide, 0.28 g (3.5 mmol) of CH3COONa, 0.87 g (13.3 mmol) of zinc dust and 5 ml of glacial acetic acid were treated as described in example 1. The residue was purified by flash chromatography (CH2Cl2 /MeOH/conc. NH4 OH 86: 10:0.6; Rf=0.27), to yield 0.2 g of the title compound.M.p.=153°-155° C. dec.

Workup

  1. customThe residue was purified by flash chromatography (CH2Cl2 /MeOH/conc. NH4 OH 86: 10:0.6; Rf=0.27)

Sources & evidence

ORD record
ord-a50aa20c2f95459b844fc6848f1ecb10
Source dataset
uspto-grants-1998_03
Patent number
US05731322

Reaction notes

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