3-(1-Methylpyrrolidin-2-yl)pyridin-2(1h)-one → (+/-)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

HRID 37451

Reaktionsgleichung

Reaktionsgleichung von HRID 37451
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]1[C:8](=[O:13])[NH:9][CH:10]=[CH:11][CH:12]=1.[C:14]([O:17][C@@H:18]1[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:22]([O:28][C:29](=[O:31])[CH3:30])[C@@H:21]([CH2:32][O:33][C:34](=[O:36])[CH3:35])[O:20][CH:19]1Br)(=[O:16])[CH3:15].[Al]>ClCCl.C(=O)([O-])[O-].[Ag+2]>[C:14]([O:17][C@@H:18]1[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:22]([O:28][C:29](=[O:31])[CH3:30])[C@@H:21]([CH2:32][O:33][C:34](=[O:36])[CH3:35])[O:20][C@H:19]1[O:13][C:8]1[C:7]([CH:3]2[CH2:4][CH2:5][CH2:6][N:2]2[CH3:1])=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:16])[CH3:15]

Komponenten

6

Edukt 3

HCID 2498843-(1-Methylpyrrolidin-2-yl)pyridin-2(1h)-oneHCID 5359268AluminumHCID 11729291Tetra-O-acetylglucopyranosyl bromide

Produkt 1

HCID 15293694(+/-)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418647HCID 178418647, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(±)-3-(1-methyl-2-pyrrolidinyl)-2-pyridone (1)(2.0 g) and 2,3,4,6-tetra-O-acetylglucopyranosyl bromide (4a)(5.6 g) were dissolved in dichloromethane (40 ml). To this solution, silver carbonate (1.8 g) was added. The mixture was stirred at room temperature for 24 hours while the vessel was shielded from light by an aluminum sheet. Solid material was filtered off, and the filtrate was concentrated under reduced pressure. As a result, (±)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (5a) was obtained. The compound (5a) obtained as above was subjected to the experiment of the following example without purification.

Aufarbeitung

  1. filtrationSolid material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-76d9c04f80b54661bd4b875a3ac88b7c
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420286

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