Dimethylformamide dimethyl acetal → tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

HRID 550792Notes

Reaction equation

HRID 550792 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[O:14])[C:12](=[CH:17][N:18]([CH3:20])[CH3:19])[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 53395404tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

Procedure

A mixture of 1-tert-butoxycarbonylpiperidin-4-one and N,N-dimethylformamide dimethylacetal was heated under reflux with stirring for 6 hours to yield 1-tert-butoxycarbonyl-3-[(dimethylamino)methylene]piperidin-4-one. A mixture of 1-tert-butoxycarbonyl-3-[(dimethylamino)methylene]piperidin-4-one obtained, 2-hydrazinoethanol, and MeOH was heated under reflux with stirring for 2 hours to yield a mixture of 2-(5-tert-butoxycarbonyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-2-yl)ethanol and 2-(5-tert-butoxycarbonyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-1-yl)ethanol. A mixture of the compounds obtained, 4M HCl-EtOAc solution, and EtOH was stirred at ambient temperature for 2 hours to yield a mixture of 2-(4,5,6,7-tetrahydro-2H-pyrazolo[4,3-c]pyridin-2-yl)ethanol dihydrochloride and 2-(4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-1-yl)ethanol dihydrochloride.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux

Sources & evidence

ORD record
ord-59efd78fe923436a908703d4432108db
Source dataset
uspto-grants-2011_05
Patent number
US07947690B2

Reaction notes

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