Hydrazine hydrate (1:1) → HCID 178453171, compound

HRID 1912453Notes

Reaction equation

HRID 1912453 reaction equation
O.[NH2:2][NH2:3].[C:4]([O:8][C:9](=[O:24])[NH:10][C:11]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[CH:18]=1)([CH3:16])[C:12](=O)[C:13]#[CH:14])([CH3:7])([CH3:6])[CH3:5]>CCO>[C:4]([O:8][C:9](=[O:24])[NH:10][C:11]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[CH:18]=1)([C:12]1[CH:13]=[CH:14][NH:3][N:2]=1)[CH3:16])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 87170226HCID 87170226, compound

Product 1

HCID 178453171HCID 178453171, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (2.48 mL, 51.10 mmol) was added to a solution of rac-[1-(3-bromo-phenyl)-1-methyl-2-oxo-but-3-ynyl]-carbamic acid tert-butyl ester (1.8 g, 5.11 mmol) in EtOH (30 mL) and the mixture was stirred at room temperature for 1 hour. The solvent was removed in vacuo and the residue was dissolved in DCM and washed with water. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 0/100 to 50/50). The desired fractions were collected and concentrated in vacuo to yield rac-[1-(3-bromo-phenyl)-1-(1H-pyrazol-3-yl)-ethyl]-carbamic acid tert-butyl ester (1.62 g, 87% yield) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with water
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvents evaporated in vacuo
  8. customThe crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 0/100 to 50/50)
  9. customThe desired fractions were collected
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a9eb0890fed142e583eddcbbb56c8c04
Source dataset
uspto-grants-2013_12
Patent number
US08609660B2

Reaction notes

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