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

HRID 1019275

Reaction equation

HRID 1019275 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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 %.

Workup

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

Sources & evidence

ORD record
ord-2476a7be6d9a462ab17e5960b19fd87f
Source dataset
uspto-grants-2002_11
Patent number
US06486323B1

Linked notes

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