Hydrazine → 5-Boc-1,4,6,7-tetrahydropyrazolo[4,3-C]pyridine

HRID 1713161Notes

Reaction equation

HRID 1713161 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[C:10](=[CH:15][N:16](C)C)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:19]N>CCO>[NH:19]1[C:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][C:10]=2[CH:15]=[N:16]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 53395404tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

Product 1

HCID 103986805-Boc-1,4,6,7-tetrahydropyrazolo[4,3-C]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl-3-[(dimethylamino)methylene]-4-oxopiperidine-1-carboxylate (63.6 g, 250 mmol) in EtOH (200 mL) is added hydrazine (9.6 mL, 305 mmol) and the mixture is heated at reflux for 2 hr. Solvent is evaporated in vacuo and residue is purified by flash column with 5% MeOH in DCM to give the title compound as a white solid. MS (M+1): 224.1.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 2 hr
  3. customSolvent is evaporated in vacuo and residue
  4. customis purified by flash column with 5% MeOH in DCM

Sources & evidence

ORD record
ord-41b6dfe29a274be685388c6d0a8cf4de
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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