(+/-)-trans-2-Ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride → (+/-)-trans-6-Ethyl-2-ethoxycarbonyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-3-trifluoromethyl-1H-pyrrolo[2,3-g]isoquinoline
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](OC)[CH:15]=3)[C@@H:6]([CH2:7][CH2:8][C:9](=O)[CH2:10]2)[CH2:5]1)[CH3:3].C1(N[N:30]=[C:31]([C:37](=O)[C:38]([F:41])([F:40])[F:39])[C:32]([O:34][CH2:35][CH3:36])=[O:33])C=CC=CC=1.C[C:44](O[Na])=[O:45]>[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:45][CH3:44])[CH:15]=3)[C@H:6]([CH2:7][C:8]3[C:37]([C:38]([F:39])([F:40])[F:41])=[C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[NH:30][C:9]=3[CH2:10]2)[CH2:5]1)[CH3:3]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
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, 8.65 g (30 mmol) of ethyl 2-phenylhydrazono-4,4,4-trifluoro-3-oxobutyrate, 2.46 g (30 mmol) of CH3COONa, 7.85 g (120 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 EtOAc/MeOH 0%→10%) yielding 3.0 g of product which was triturated in Et2O yielding 2.5 g of the title compound. M.p. 209°-211° C.
Workup
- customThe residue was purified by chromatography on silica gel EtOAc/MeOH 0%→10%)
Sources & evidence
- ORD record
- ord-e47c72c20e604a20b47414090524ffc6
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05731322
Reaction notes
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