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

HRID 2860

Reaction equation

HRID 2860 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)[CH3:38])[C:32]([O:34][CH2:35][CH3:36])=[O:33])C=CC=CC=1.C[C:41](O[Na])=[O:42]>C(O)(=O)C.[Zn]>[CH2:2]([N:4]1[CH2:13][CH2:12][C@:11]2([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:42][CH3:41])[CH:15]=3)[C@H:6]([CH2:7][C:8]3[C:37]([CH3:38])=[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

HCID 86752325(+/-)-trans-2-Ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochlorideHCID 178418247HCID 178418247, compoundHCID 178418256HCID 178418256, compound

Product 1

HCID 22883674(+/-)-trans-6-Ethyl-2-ethoxycarbonyl-3-methyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinolineYield 61.3%

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 and 0.87 g (93.7 mmol) of ethyl 2-phenylhydrazono-3-oxobutyrate [Organic Reactions, R. Adams Ed; Wiley, New York, 10, 32-33, (1951-1959)] were dissolved in a mixture of 3 mi of glacial acetic acid and 0.34 g (4.2 mmol) of CH3COONa. The solution was treated as described in example 1 adding 0.74 g (11.3 mmol) of zinc dust. The residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 94:5:0.5; Rf=0.3), obtaining 0.6 g of the title compound.

Workup

  1. additionThe solution was treated
  2. customThe residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 94:5:0.5; Rf=0.3)

Sources & evidence

ORD record
ord-ceee2b4669514a49ad828e34aae4470f
Source dataset
uspto-grants-1998_03
Patent number
US05731322

Linked notes

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