Sodium borohydride → HCID 10473616, compound

HRID 2184085Notes

Reaction equation

HRID 2184085 reaction equation
[CH3:1][N:2]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=1)[CH2:3][C:4](=[O:8])[CH2:5][CH2:6][CH3:7].[BH4-].[Na+]>CO>[CH3:1][N:2]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:24])([C:20]([F:22])([F:23])[F:21])[C:16]([F:17])([F:18])[F:19])=[CH:11][CH:10]=1)[CH2:3][CH:4]([OH:8])[CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10089688HCID 10089688, compound

Product 1

HCID 10473616HCID 10473616, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(methyl{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)-ethyl]phenyl}amino)-pentan-2-one (52 mg, 0.15 mmol) in methanol (3 mL) at −78° C. was added sodium borohydride (17 mg, 0.44 mmol). The reaction mixture was allowed to warm to ambient temperature over 4 hours. The reaction mixture was quenched with water and extracted twice with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography (4:1 hexanes/EtOAc) afforded the title compound as a colorless oil (40 mg, 74%). 1H NMR (CDCl3) δ 7.51 (d, 2H), 6.80 (d, 2H), 3.96 (m, 1H), 3.32 (s, 1H), 3.30 (dq, 2H), 3.03 (s, 3H), 1.39-1.52 (m, 4H), 0.96 (t, 3H). 13C NMR (CDCl3) δ 151.0, 127.4, 116.8, 112.1, 69.4, 60.0, 39.3, 36.8, 18.9, 14.1. MS (ES+) m/z 360 (MH+).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted twice with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (4:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-febc75528fa140288c5af3c3d6c51ca1
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

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