Methylamine → Dimethyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2,4-dicarboxylate

HRID 1019275

Reaktionsgleichung

Reaktionsgleichung von HRID 1019275
[CH2:1]([CH:5]=O)[CH2:2][CH:3]=O.[CH3:7][O:8][C:9]([CH2:11][C:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:13])=[O:10].[CH3:19][NH2:20]>CO>[CH3:19][N:20]1[CH:3]2[CH2:2][CH2:1][CH:5]1[CH:11]([C:9]([O:8][CH3:7])=[O:10])[C:12](=[O:13])[CH:14]2[C:15]([O:17][CH3:18])=[O:16]

Komponenten

5

Edukt 3

HCID 6329MethylamineHCID 12524Butanedial2×HCID 74591Dimethyl 3-oxoglutarate

Produkt 1

HCID 251888Dimethyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2,4-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The reaction of succindialdehyde of the formula (3) with the organic amine of the formula (4) and the acetonedicarboxylic acid ester of the formula (5) is per se well known. For example, when each of the substitu-ents R and R″ is a methyl group (Me), a methanolic solution containing dimethyl 1,3-acetonedicarboxylate is added to a methanol solution of succindialdehyde in an ice bath under a nitrogen atmosphere, a methanolic solution containing methylamine is added dropwise thereto in an ice bath and stirred overnight, and the solvent is distilled off to obtain dimethyl 8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-2,4-dicarboxylate (1a: R′=Me and R=Me in the formula (1)) in a yield of 70-90 mol %.

Aufarbeitung

  1. additionis added dropwise
  2. distillationthe solvent is distilled off

Quellen und Nachweise

ORD-Eintrag
ord-2476a7be6d9a462ab17e5960b19fd87f
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06486323B1

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