Sodium Hydroxide → (S)-1-(4-methoxybenzyl)-octahydroisoquinoline

HRID 4696Notes

Reaction equation

HRID 4696 reaction equation
C([O-])(=O)C.[CH3:5][O:6][C:7]1[CH:23]=[CH:22][C:10]([CH2:11][C@H:12]2[C:21]3[CH:16]([CH2:17][CH2:18][CH2:19][CH:20]=3)[CH2:15][CH2:14][NH2+:13]2)=[CH:9][CH:8]=1.[OH-].[Na+]>O>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][C@H:12]2[C:21]3[CH:16]([CH2:17][CH2:18][CH2:19][CH:20]=3)[CH2:15][CH2:14][NH:13]2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18611875(S)-1-(4-methoxybenzyl)-octahydroisoquinolinium acetate

Product 1

HCID 18611876(S)-1-(4-methoxybenzyl)-octahydroisoquinolineYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 31.7 g of (S)-1-(4-methoxybenzyl)-octahydroisoquinolinium acetate in 250 ml of water is brought by addition of concentrated sodium hydroxide solution to pH 12. The free base is extracted twice with 150 ml of diethyl ether each time. Washing of the combined extracts with water, drying over sodium sulfate and removal of the solvent in vacuo leaves 25.0 g (97.3% of theory) of (S)-1-(4-methoxybenzyl)-octahydroisoquinoline.

Workup

  1. extractionThe free base is extracted twice with 150 ml of diethyl ether each time
  2. washWashing of the combined extracts with water
  3. dry with materialdrying over sodium sulfate and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-8be19d99101940f8b611464ff0ecf239
Source dataset
uspto-grants-1988_02
Patent number
US04727147

Reaction notes

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