Borane;tetrahydrofuran → 1-(4-bromo-1-methyl-1H-pyrazol-3-yl)-4-(hydroxymethyl)pyrrolidin-2-one

HRID 632768Notes

Reaction equation

HRID 632768 reaction equation
[Br:1][C:2]1[C:3]([N:8]2[C:12](=[O:13])[CH2:11][CH:10]([C:14](O)=[O:15])[CH2:9]2)=[N:4][N:5]([CH3:7])[CH:6]=1.B.C1COCC1>C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([N:8]2[CH2:9][CH:10]([CH2:14][OH:15])[CH2:11][C:12]2=[O:13])=[N:4][N:5]([CH3:7])[CH:6]=1

Participants

5

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 1180618811-(4-bromo-1-methyl-1H-pyrazol-3-yl)-5-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 1180616531-(4-bromo-1-methyl-1H-pyrazol-3-yl)-4-(hydroxymethyl)pyrrolidin-2-oneYield 17.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-bromo-1-methyl-1H-pyrazol-3-yl)-5-oxopyrrolidine-3-carboxylic acid (511 mg) obtained in Step A of Example 7 in THF (3.0 mL) was added 1.1M borane-THF complex THF solution (5.0 mL) under ice-cooling. The reaction mixture was stirred at room temperature for 20 hr, and diluted with ethyl acetate. The diluted solution was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and (methanol/ethyl acetate) to give the title compound (84 mg).

Workup

  1. temperaturecooling
  2. washThe diluted solution was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane) and (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-981ed927dfa94ba9ae68a3d35e028ae1
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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