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

HRID 4696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 4696
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 18611876(S)-1-(4-methoxybenzyl)-octahydroisoquinolineAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8be19d99101940f8b611464ff0ecf239
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727147

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