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

HRID 2875Notes

Reaction equation

HRID 2875 reaction equation
Cl.C([N:4]1[CH2:13][CH2:12][C@@:11]2(C3C=CC=C(OC)C=3)[C@@H:6]([CH2:7][CH2:8][C:9](=O)[CH2:10]2)[CH2:5]1)C.C[N:24](C)[C:25](=O)[C:26](=NNC1C=CC=CC=1)[C:27](=O)C.CC(O[Na])=O>[Zn].C(O)(=O)C>[CH3:27][C:26]1[C:8]2[CH2:7][CH:6]3[CH:11]([CH2:12][CH2:13][NH:4][CH2:5]3)[CH2:10][C:9]=2[NH:24][CH:25]=1

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 178418387HCID 178418387, compound

Product 1

HCID 189361993-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinolineYield 84.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

1.0 g (3.1 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 2.33 g (10 mmol) of N, N-dimethyl-2-phenylhydrazono-3-oxobutyramide, 0.82 g (1 0 mmol) of CH3COONa, 2.6 g (40 mmol) of zinc dust and 5 ml of glacial acetic acid were treated as described in example 1. The residue was purified by chromatography on silica gel (EtOAc/MeOH 0%→30%) yielding 0.5 g of product which was crystallized from Et2O yielding 0.5 g of the title compound. M.p.=151°-153° C.

Workup

  1. customThe residue was purified by chromatography on silica gel (EtOAc/MeOH 0%→30%)

Sources & evidence

ORD record
ord-53e465a32b0c4c70bcd0b9d12d1a9382
Source dataset
uspto-grants-1998_03
Patent number
US05731322

Reaction notes

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