Water → HCID 68156412, compound

HRID 1892689Notes

Reaction equation

HRID 1892689 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][C:4]([C:6]1[CH:7]=[N:8][C:9]([N:12]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[N:13]2)=[CH:10][CH:11]=1)=[O:5].[BH4-].[Na+].O>CO>[CH3:1][CH:2]([CH3:21])[CH2:3][CH:4]([C:6]1[CH:7]=[N:8][C:9]([N:12]2[CH:16]=[C:15]([C:17]([F:19])([F:18])[F:20])[CH:14]=[N:13]2)=[CH:10][CH:11]=1)[OH:5]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 68156487HCID 68156487, compound

Product 1

HCID 68156412HCID 68156412, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a 0° C. solution of 3-methyl-1-(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)butan-1-one (1.4 g, 4.7 mmol) in methanol (20 mL) was added sodium borohydride (367 mg, 9.4 mmol). The resulting mixture was stirred at 20° C. for 1 hour. Water was added and the mixture was extracted with ethyl acetate (40 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to give 3-methyl-1-(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)butan-1-ol (1.4 g) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 8.78 (s, 1H), 8.32 (d, J=2.0 Hz, 1H), 7.91 (d, J=8.4 Hz, 1H), 7.82-7.79 (m, 2H), 4.82-4.77 (m, 1H), 1.83 (s, 1H), 1.75-1.64 (m, 2H), 1.47-1.43 (m, 1H), 0.88-0.92 (m, 6H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (40 mL)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-725ca766f37e4929863d02ab1a5fc6ac
Source dataset
uspto-grants-2013_08
Patent number
US08507533B2

Reaction notes

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