Methanol → trans-(2S)-1-(4-Benzo[b]furanoxy)-3-(2-methyl-4-(4-methylbenzothiazol-2-yl)piperidin-1-yl)-2-propanol Oxalate

HRID 1760630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1760630
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[S:15][C:16]3[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:17]=3[N:18]=2)=[CH:10][CH:9]1[CH3:24])=[O:7])(C)(C)C.[O:25]1[CH2:27][C@H:26]1[CH2:28][O:29][C:30]1[C:38]2[CH:37]=[CH:36][O:35][C:34]=2[CH:33]=[CH:32][CH:31]=1.C[OH:40]>>[C:36]([OH:35])(=[O:40])[C:6]([OH:5])=[O:7].[O:35]1[CH:36]=[CH:37][C:38]2[C:30]([O:29][CH2:28][C@@H:26]([OH:25])[CH2:27][N:8]3[CH2:13][CH2:12][C@@H:11]([C:14]4[S:15][C:16]5[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:17]=5[N:18]=4)[CH2:10][C@@H:9]3[CH3:24])=[CH:31][CH:32]=[CH:33][C:34]1=2

Komponenten

4

Edukt 3

HCID 887MethanolHCID 20659907(S)-(+)-4-(oxiranylmethoxy)benzo[b]furanHCID 225958521-(t-Butyloxycarbonyl)-4-(4-methylbenzothiazol-2-yl)-2-methyl-1,2,5,6-tetrahydropyridine

Produkt 1

HCID 69739947trans-(2S)-1-(4-Benzo[b]furanoxy)-3-(2-methyl-4-(4-methylbenzothiazol-2-yl)piperidin-1-yl)-2-propanol Oxalate

Versuchsvorschrift

A solution of trans-4-(4-methylbenzothiazol-2-yl)-2-methylpiperidine (0.061 g, 0.248 mmol, prepared in example 24) and (S)-(+)-4-(oxiranylmethoxy)benzo[b]furan (0.047 g, 0.248 mmol) in methanol (3 mL) was heated at reflux for 18 hours and then cooled and evaporated. The residue was purified using silica gel chromatography (dichloromethane/2% methanol/0.2% ammonium hydroxide in dichloromethane gradient elution) to give the free bases of the title compounds as two separate yellow oils. The oxalate salts were prepared to give the title compounds.

Aufarbeitung

  1. temperatureat reflux for 18 hours
  2. temperaturecooled
  3. customevaporated
  4. customThe residue was purified
  5. washsilica gel chromatography (dichloromethane/2% methanol/0.2% ammonium hydroxide in dichloromethane gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-61958b1e7e134f83b2c7d611609910fa
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06844344B2

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