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

HRID 1353555Notes

Reaction equation

HRID 1353555 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-d7b0a414e4184bbdbd939bc6510d2b92
Source dataset
uspto-grants-2007_05
Patent number
US07220862B2

Reaction notes

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