Acetic Anhydride → (RS)-Salsolinol

HRID 6757

Reaktionsgleichung

Reaktionsgleichung von HRID 6757
C(O[C:5](=[O:7])[CH3:6])(=O)C.[C:8](Cl)(=[O:11])[CH2:9][CH3:10].C[O:14][C:15]1C=[CH:19][C:18]([NH:21][CH2:22][CH3:23])=[CH:17][CH:16]=1.CO[C:26]1[CH:27]=[C:28]([CH2:34][CH2:35][NH2:36])[CH:29]=[CH:30][C:31]=1[O:32]C.[CH3:37][C:38]1[CH:39]=[C:40]([CH2:46][CH2:47][NH2:48])[CH:41]=[CH:42][C:43]=1OC>>[CH2:9]([CH:10]1[C:29]2[C:28](=[CH:27][CH:26]=[C:31]([OH:32])[CH:30]=2)[CH2:34][CH2:35][NH:36]1)[CH3:8].[CH3:19][CH:18]1[C:17]2[C:10](=[CH:9][C:8]([OH:11])=[C:15]([OH:14])[CH:16]=2)[CH2:23][CH2:22][NH:21]1.[CH3:37][CH:38]1[C:39]2[C:40](=[CH:41][C:42]([CH3:43])=[C:5]([OH:7])[CH:6]=2)[CH2:46][CH2:47][NH:48]1

Komponenten

8

Edukt 5

HCID 7918Acetic AnhydrideHCID 8421HomoveratrylamineHCID 62324Propionyl chlorideHCID 64846602-(4-Methoxy-3-methylphenyl)ethan-1-amineHCID 11804947N-Ethyl-4-methoxybenzenamine

Produkt 3

HCID 54456(RS)-SalsolinolHCID 220184881,6-Dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-olHCID 220185211-Ethyl-1,2,3,4-tetrahydro-isoquinolin-7-ol

Versuchsvorschrift

Similarly, 1-ethyl-1,2,3,4-tetrahydro-isoquinolin-7-ol was prepared by the above procedures by replacing the acetic anhydride in Procedure EEE with propionyl chloride. 1-Methyl-1,2,3,4-tetrahydro-isoquinoline-6,7-diol and 1,6-dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-ol were prepared by replacing the (4-methoxy-phenyl)-ethylamine in procedure EEE with 3,4-dimethoxyphenylethylamine and 3-methyl-4-methoxyphenylethylamine, respectively.

Quellen und Nachweise

ORD-Eintrag
ord-e7cbb3815910472891528b46b72c15cf
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084154B2

Verknüpfte Notizen

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