Ammonium Chloride → (2R)-4-hydroxy-2-methyl-N-(1-methyl-1H-pyrazol-3-yl)butanamide

HRID 632795Notes

Reaction equation

HRID 632795 reaction equation
[BH4-].[Li+].[CH3:3][C@@H:4]([C:10]([NH:12][C:13]1[CH:17]=[CH:16][N:15]([CH3:18])[N:14]=1)=[O:11])[CH2:5][C:6](OC)=[O:7].[Cl-].[NH4+]>C1COCC1.CO>[OH:7][CH2:6][CH2:5][C@@H:4]([CH3:3])[C:10]([NH:12][C:13]1[CH:17]=[CH:16][N:15]([CH3:18])[N:14]=1)=[O:11]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 118065287methyl (3R)-3-methyl-4-((1-methyl-1H-pyrazol-3-yl)amino)-4-oxobutanoate

Product 1

HCID 118060904(2R)-4-hydroxy-2-methyl-N-(1-methyl-1H-pyrazol-3-yl)butanamideYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of lithium borohydride (97 mg) in THF (5.0 mL) was added a solution of methyl (3R)-3-methyl-4-((1-methyl-1H-pyrazol-3-yl)amino)-4-oxobutanoate (240 mg) in methanol (1.0 mL) under ice-cooling. The reaction mixture was stirred at room temperature for 2 hr, saturated aqueous ammonium chloride solution was added thereto, and the mixture was extracted with ethyl acetate. The extract 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) to give the title compound (208 mg).

Workup

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

Sources & evidence

ORD record
ord-89260389991c47a2bace8fa29c36824e
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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