Methylhydrazine → (S)-t-Butyl 2-(5-((3,4-dimethoxyphenoxy)methyl)-1-methyl-1H-pyrazol-3-yl)pyrrolidine-1-carboxylate

HRID 710051Notes

Reaction equation

HRID 710051 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[O:6][CH2:7][C:8]#[C:9][C:10]([C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=O.[CH3:29][NH:30][NH2:31].C([O-])(=O)C.[Na+]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[O:6][CH2:7][C:8]1[N:30]([CH3:29])[N:31]=[C:10]([C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:9]=1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 517045Sodium AcetateHCID 86706763HCID 86706763, compound

Product 1

HCID 86706764(S)-t-Butyl 2-(5-((3,4-dimethoxyphenoxy)methyl)-1-methyl-1H-pyrazol-3-yl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an EtOH (5.0 mL) solution of the compound (390 mg) obtained in Example 13-(1), methylhydrazine (106 μL) and sodium acetate (246 mg) were added and the mixture was heated under reflux for 20 hours. The reaction mixture was concentrated and a saturated aqueous solution of NH4Cl (50 mL) was added to separate the organic layer, which was dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by neutral silica gel chromatography (AcOEt/hexane) to give the titled compound (378 mg, pale brown oil.)

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 20 hours
  3. concentrationThe reaction mixture was concentrated
  4. additiona saturated aqueous solution of NH4Cl (50 mL) was added
  5. customto separate the organic layer, which
  6. dry with materialwas dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a crude product, which
  10. customwas further purified by neutral silica gel chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-c7322e05fdb34bda974bb72d5a3a5efb
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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