Potassium Formate → HCID 117942044, compound

HRID 1499127Notes

Reaction equation

HRID 1499127 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.C([O-])=O.[K+]>CC#N.[Ir].O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:14]([OH:19])[C:15]([F:17])([F:18])[F:16])=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=1

Participants

6

Reactant 2

HCID 2735122Potassium FormateHCID 117952235HCID 117952235, compound

Product 1

HCID 117942044HCID 117942044, compound

Reagents, catalysts & solvents 3

HCID 23924IridiumCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

1-(5-Bromo-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethanone (1.3 g, 3.9 mmol) in CH3CN (10 mL) was reduced to the chiral alcohol using the chiral iridium catalyst (METHOD A) at RT. The reaction mixture was then charged with potassium formate (725 mg, 8.6 mmol) and the mixture was stirred at 40° C. for 12 h. Then the reaction was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered, concentrated in vacuo and purified by normal phase silica gel column (EtOAc:PE=1:10) to afford the title compound as a colorless oil.

Workup

  1. customat RT
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by normal phase silica gel column (EtOAc:PE=1:10)

Sources & evidence

ORD record
ord-9118036949a5485397951bc7ddb75828
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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