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

HRID 2250205Notes

Reaction equation

HRID 2250205 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-6b617a005ecf4566b4a9b27e1e750143
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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