tert-butyl (3R)-3-{[3-chloro-5-(hydroxymethyl)-2-pyridinyl]amino}-1-pyrrolidinecarboxylate → tert-butyl (3R)-3-[(3-chloro-5-formyl-2-pyridinyl)amino]-1-pyrrolidinecarboxylate

HRID 226425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 226425
[Cl:1][C:2]1[C:3]([NH:10][C@@H:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]2)=[N:4][CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1>CCOC(C)=O.O=[Mn]=O>[Cl:1][C:2]1[C:3]([NH:10][C@@H:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]2)=[N:4][CH:5]=[C:6]([CH:8]=[O:9])[CH:7]=1

Komponenten

4

Edukt 1

HCID 86603728tert-butyl (3R)-3-{[3-chloro-5-(hydroxymethyl)-2-pyridinyl]amino}-1-pyrrolidinecarboxylate

Produkt 1

HCID 86603729tert-butyl (3R)-3-[(3-chloro-5-formyl-2-pyridinyl)amino]-1-pyrrolidinecarboxylateAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl (3R)-3-{[3-chloro-5-(hydroxymethyl)-2-pyridinyl]amino}-1-pyrrolidinecarboxylate (0.95 g) and MnO2 (3.02 g) in AcOEt (30 ml) was refluxed under stirring for 1.5 hours. After removal of the insoluble material, and the solvent was evaporated in vacuo to give tert-butyl (3R)-3-[(3-chloro-5-formyl-2-pyridinyl)amino]-1-pyrrolidinecarboxylate (0.95 g).

Aufarbeitung

  1. temperaturewas refluxed
  2. customAfter removal of the insoluble material
  3. customthe solvent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fca4f9c2dfab42f2a1d7c0f0faaf07f2
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557127B2

Notizen zur Reaktion

Wird geladen…