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

HRID 2355893Notes

Reaction equation

HRID 2355893 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].O.[NH2:20]N>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[NH:20][N:16]=[CH:15][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 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 887MethanolSolvent

Procedure

To a solution of 3-dimethylaminomethylene-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (2.55 g, 10 mmol) in methanol (50 mL) was added hydrazine hydrate (0.61 mL, 1.25 equiv). The solution was heated to reflux, immediately allowed to cool to room temperature, and concentrated to give 1.4 g (63%) which was used without purification. Mass spec.: 224.11 (MH)+.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. concentrationconcentrated
  4. customto give 1.4 g (63%) which
  5. customwas used without purification

Sources & evidence

ORD record
ord-b6e2243cc04644598385a5f7cec7b162
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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