Methanol → 1-(4-fluoro-phenyl)-5-hydroxymethyl-4-isopropyl-1H-pyrazole-3-carboxylic acid benzylamide
Reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[C:15]([CH:16]([CH3:18])[CH3:17])=[C:14]([CH:19]=[O:20])[N:13]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[N:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[BH4-].[Na+]>C1COCC1>[CH2:1]([NH:8][C:9]([C:11]1[C:15]([CH:16]([CH3:18])[CH3:17])=[C:14]([CH2:19][OH:20])[N:13]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[N:12]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1-(4-fluoro-phenyl)-5-formyl-4-isopropyl-1H-pyrazole-3-carboxylic acid benzylamide (0.620 g, 1.70 mmol) in THF:MeOH (40 mL) at 0° C. was added sodium borohydride (96.3 mg, 2.55 mmol; commercially available from Sigma Aldrich). The reaction was stirred for 30 min at 0° C. at which point TLC analysis indicated the reaction was complete and the solvent was removed under reduced pressure. To the reaction residue was added ethyl acetate (50 mL) and saturated NaHCO3 (15 mL), and the organic layer was separated, dried (Na2SO4) and concentrated. The resulting oil was purified by silica gel chromatography (40% EtOAc/Hex) to afford 1-(4-fluoro-phenyl)-5-hydroxymethyl-4-isopropyl-1H-pyrazole-3-carboxylic acid benzylamide (0.540 g, 87%): MS(APCI+): m/z368.1 (M+H).
Workup
- customthe solvent was removed under reduced pressure
- additionTo the reaction residue was added ethyl acetate (50 mL) and saturated NaHCO3 (15 mL)
- customthe organic layer was separated
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe resulting oil was purified by silica gel chromatography (40% EtOAc/Hex)
Sources & evidence
- ORD record
- ord-33bc7a7faa9145dea32acf8676b69123
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07446121B2
Reaction notes
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