(+/-)-trans-2-Ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride → (+/-)-trans-2-Diethylaminocarbonyl-3,6-dimethyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline
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][CH2:8][C:9](=O)[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:9]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]([CH2:7][C:8]=2[C:28]=1[CH3:29])[CH2:5][N:4]([CH3:42])[CH2:13][CH2:12]3)=[O:39])[CH3:41]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
3 g (9.3 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 2.92 g (11.2 mmol) of N,N-diethyl-2-phenylhydrazono-3-oxobutyramide, 0.92 g (11.2 mmol) of CH3COONa, 2.8 g (42.8 mmol) of zinc dust and 9.3 ml of glacial acetic acid were treated as described in example 1. The residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 90:10:1; Rf=0.27) yielding 0.56 g of the title compound. M.p. (.HCl)=250° C. dec. C25H35N3O2I.R. (KBr) (hydrochloride): 3410, 3200, 2915, 2510, 1605, 1580 cm-1.
Workup
- customThe residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 90:10:1; Rf=0.27)
Sources & evidence
- ORD record
- ord-a4e872fd5a6e4a58b4e93bf3d6bae84a
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05731322
Reaction notes
Loading…