Acetic Acid → (+/-)-trans-2-Aminocarbonyl-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline

HRID 2873Notes

Reaction equation

HRID 2873 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](CCC(=O)[CH2:10]2)[CH2:5]1)[CH3:3].C1(N[N:30]=[C:31]([C:35](=O)[CH3:36])[C:32]([NH2:34])=[O:33])C=CC=CC=1.[CH3:38][C:39](O[Na])=O.[C:43](O)(=O)C>[Zn]>[NH2:34][C:32]([C:31]1[NH:30][C:43]2[CH2:10][C@@:11]3([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=4)[C@H:6]([CH2:38][C:39]=2[C:35]=1[CH3:36])[CH2:5][N:4]([CH2:2][CH3:3])[CH2:13][CH2:12]3)=[O:33]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 86752325(+/-)-trans-2-Ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochlorideHCID 178418247HCID 178418247, compoundHCID 178418482HCID 178418482, compound

Product 1

HCID 22883638(+/-)-trans-2-Aminocarbonyl-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

3.24 g (10 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 6.16 g (30.0 mmol) of 2-phenylhydrazono-3-oxobutyramide, 2.46 g (7.0 mmol) of CH3COONa, 7.85 g (120.0 mmol) of zinc dust and 15 ml of glacial acetic acid were treated as described in example 1. The residue was purified by chromatography on silica gel (Et2O-EtOAc/MeOH 0%→50%) yielding 3.0 g of oily product which was triturated in Et2O yielding 2.5 g of the title compound. M.p.=176°-178° C.

Workup

  1. customThe residue was purified by chromatography on silica gel (Et2O-EtOAc/MeOH 0%→50%)

Sources & evidence

ORD record
ord-d4dc502d78a2417cbeb0d77e8113c760
Source dataset
uspto-grants-1998_03
Patent number
US05731322

Reaction notes

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