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

HRID 1177727Notes

Reaction equation

HRID 1177727 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-a68705da75f145578e7bf990c23f515f
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

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