Methylhydrazine → HCID 58171546, compound

HRID 1752300Notes

Reaction equation

HRID 1752300 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13](=O)[C:14]#[C:15][CH3:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][NH:19][NH2:20]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:14]=[C:15]([CH3:16])[N:19]([CH3:18])[N:20]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 58171626HCID 58171626, compound

Product 1

HCID 58171546HCID 58171546, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-(1-oxo-but-2-ynyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.8 g, 3.4 mmol) in MeOH (20 mL) was added methyl-hydrazine (5 g, 44 mmol). The mixture was stirred at room temperature for 10 hours. The reaction mixture was quenched with water (50 mL) and extracted with CH2Cl2 (50 mL×3). The combined organic layers were washed with water (30 mL) and brine (30 mL), dried over Na2SO4 and concentrated. The residue was purified by preparative TLC (PE/EA=1:1) to afford 3-(1,5-dimethyl-1H-pyrazol-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (800 mg, 88%) as white solid.

Workup

  1. customThe reaction mixture was quenched with water (50 mL)
  2. extractionextracted with CH2Cl2 (50 mL×3)
  3. washThe combined organic layers were washed with water (30 mL) and brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC (PE/EA=1:1)

Sources & evidence

ORD record
ord-837ca288a444444f85d482c3b6633bc7
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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