Hydrazine → 1'-(tert-Butoxycarbonyl)-3-oxo-2,3,4,5-tetrahydrospiro[cyclopentapyrazole-6(1H),4'-piperidine]

HRID 8754Notes

Reaction equation

HRID 8754 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH2:8][C:7]2([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[C:6]1=O)=O.[NH2:23][NH2:24]>C1(C)C=CC=CC=1>[C:18]([O:17][C:15]([N:12]1[CH2:13][CH2:14][C:7]2([C:6]3[NH:24][NH:23][C:3](=[O:2])[C:5]=3[CH2:9][CH2:8]2)[CH2:10][CH2:11]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 219838978-tert-Butyl 2-methyl 1-oxo-8-azaspiro[4.5]decane-2,8-dicarboxylate

Product 1

HCID 219839441'-(tert-Butoxycarbonyl)-3-oxo-2,3,4,5-tetrahydrospiro[cyclopentapyrazole-6(1H),4'-piperidine]Yield 61.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of tert-butyl 2-(methoxycarbonyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxate from Procedure 1, Step F (0.448 g, 1.46 mmol) in toluene (15 mL) was added hydrazine (0.084 mL, 1.72 mmol). The reaction mixture was refluxed for 12 h, concentrated and the residue was purified by flash chromatography eluting with 5% MeOH/dichloromethane and 0.1% triethylamine to give the title compound (0.263 g). MS/EI (acetonitrile/water): m/z 294.3 retention time=2.0 min.

Workup

  1. temperatureThe reaction mixture was refluxed for 12 h
  2. concentrationconcentrated
  3. customthe residue was purified by flash chromatography
  4. washeluting with 5% MeOH/dichloromethane and 0.1% triethylamine

Sources & evidence

ORD record
ord-701f21b2c1d643e889f13cae87e55dcf
Source dataset
uspto-grants-2006_08
Patent number
US07091211B2

Reaction notes

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