Reaktion #65729

ord-76d9c04f80b54661bd4b875a3ac88b7c

Reaktionsgleichung

CN1CCCC1c1ccc[nH]c1=O
(±)-3-(1-methyl-2-pyrrolidinyl)-2-pyridone
CC(=O)OC[C@H]1OC(Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
2,3,4,6-tetra-O-acetylglucopyranosyl bromide
[Al]
aluminum
→
CC(=O)OC[C@H]1O[C@@H](Oc2ncccc2C2CCCN2C)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
(±)-3-(1-methyl-2-pyrrolidinyl)-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Edukte

CN1CCCC1c1ccc[nH]c1=O
(±)-3-(1-methyl-2-pyrrolidinyl)-2-pyridone
CC(=O)OC[C@H]1OC(Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
2,3,4,6-tetra-O-acetylglucopyranosyl bromide
[Al]
aluminum

Reagenzien

O=C([O-])[O-].[Ag+2]
silver carbonate

Lösungsmittel

ClCCl
dichloromethane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationSolid material was filtered off
  2. 2
    Einengenthe filtrate was concentrated under reduced pressure

Vorschrift

(±)-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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05420286uspto-grants-1995_05