Sodium borohydride → HCID 57809766, compound

HRID 2106008Notes

Reaction equation

HRID 2106008 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([OH:28])([CH2:16][N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20](=[O:27])[CH:19]=[CH:18]1)[CH2:4][C:5]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12])([CH3:7])[CH3:6].[BH4-].[Na+]>CO.C1COCC1>[OH:28][C:3]([C:2]([F:30])([F:1])[F:29])([CH2:4][C:5]([C:8]1[CH:15]=[CH:14][CH:13]=[C:10]([CH2:11][OH:12])[CH:9]=1)([CH3:7])[CH3:6])[CH2:16][N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20](=[O:27])[CH:19]=[CH:18]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 57809733HCID 57809733, compound

Product 1

HCID 57809766HCID 57809766, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the 3-[4,4,4-trifluoro-3-hydroxy-1,1-dimethyl-3-(4-oxo-4H-quinolin-1-ylmethyl)butyl]benzaldehyde (20.0 mg, 0.05 mmol) in methanol (0.50 mL) and THF (0.50 mL) was added NaBH4 (20.0 mg, 0.48 mmol). The reaction vessel was sealed and stirred for 45 minutes. The solvent was evaporated in vacuo and the off-white solid was re-dissolved in EtOAc and water and transferred to a separatory funnel. The aqueous layer was extracted with two 10 mL portions of EtOAc and the combined organic layers were washed with one 10 mL portion of brine, dried over magnesium sulfate, filtered, and the solvent was evaporated in vacuo to give a white foam. The material was chromatographed (6% MeOH/CH2Cl2, 0.5% NH4OH) to give the desired compound, 1-[2-hydroxy-4-(3-hydroxymethylphenyl)-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one as a white foam (6.6 mg, 36%).

Workup

  1. customThe reaction vessel was sealed
  2. customThe solvent was evaporated in vacuo
  3. dissolutionthe off-white solid was re-dissolved in EtOAc
  4. customwater and transferred to a separatory funnel
  5. extractionThe aqueous layer was extracted with two 10 mL portions of EtOAc
  6. washthe combined organic layers were washed with one 10 mL portion of brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated in vacuo
  10. customto give a white foam
  11. customThe material was chromatographed (6% MeOH/CH2Cl2, 0.5% NH4OH)

Sources & evidence

ORD record
ord-cfb5339b1263406a9d2208e271514d34
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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