Aluminium lithium hydride → N-(4-Phenyl-n-butyl)-4a-(m-methoxyphenyl)-cis-decahydroisoquinoline

HRID 26474Notes

Reaction equation

HRID 26474 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][N:11]2[C:20](=O)[CH2:19][C@@:18]3([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=4)[C@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]3)[C:12]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:20][CH2:19][C@@:18]3([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=4)[C@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]3)[CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86736476N-(4-Phenyl-n-butyl)-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

Product 1

HCID 86736475N-(4-Phenyl-n-butyl)-4a-(m-methoxyphenyl)-cis-decahydroisoquinolineYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-Phenyl-n-butyl)-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline (0.8 g) in anhydrous tetrahydrofuran was treated with 0.8 g of lithium aluminum hydride and refluxed overnight. The reaction mixture was worked up as indicated in Example 2-B to yield 0.7 g of an opaque oil which was evaporatively distilled, bp 80°-90°, and identified as N-(4-phenyl-n-butyl)-4a-(m-methoxyphenyl)-cis-decahydroisoquinoline.

Workup

  1. temperaturerefluxed overnight

Sources & evidence

ORD record
ord-5718360a5f0e477b9758c10416f4c28f
Source dataset
uspto-grants-1979_04
Patent number
US04150135

Reaction notes

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