Methanol → Methyl cis-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate

HRID 382809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 382809
[CH2:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH:11]2[CH2:12][N:13]([CH3:22])[CH2:14][CH2:15]/[C:16]/2=[CH:17]\[C:18]([O:20][CH3:21])=[O:19])=[CH:5][C:4]=1[O:23][CH3:24])[CH3:2].[H][H].[CH3:27][OH:28]>[Pd]>[C:18]([O:20][CH2:21][CH3:27])(=[O:19])[CH3:17].[CH3:8][OH:9].[NH4+:13].[OH-:28].[CH2:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C@H:11]2[C@@H:16]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:15][CH2:14][N:13]([CH3:22])[CH2:12]2)=[CH:5][C:4]=1[O:23][CH3:24])[CH3:2].[CH2:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C@H:11]2[C@H:16]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:15][CH2:14][N:13]([CH3:22])[CH2:12]2)=[CH:5][C:4]=1[O:23][CH3:24])[CH3:2]

Komponenten

7

Edukt 3

HCID 887MethanolHCID 86757543methyl (E)-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-ylidene]acetateHCID 178418361HCID 178418361, Verbindung

Produkt 3

HCID 21901312Ethyl acetate methanol ammonium hydroxideHCID 69823052Methyl trans-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetateAusbeute 21 %HCID 69823475Methyl cis-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

g 2) A solution of 11.7 g (35.3 mmol) of methyl (E)-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-ylidene]acetate in 100 ml of methanol was treated with 500 mg of Pd on charcoal and hydrogenated with hydrogen at room temperature for 12 hours. The catalyst was filtered off and the filtrate was evaporated. Chromatography (silica gel, ethyl acetate/methanol/NH4OH 200:10:1) yielded 9.14 g (77%) of methyl cis-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate as a colorless oil, Rf=0.23 (silica gel ethyl acetate methanol/NH4OH 200:10:1) and 2.56 g (21%) of methyl trans-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate as a colorless oil, Rf=0.12 (silica gel, ethyl acetate/methanol/NH4OH 200:10:1).

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-10d2d1a2c6cc448f879dc2afd98ac5e9
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310208B1

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