Vertellus → HCID 86732222, compound

HRID 930391Notes

Reaction equation

HRID 930391 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@:9]([NH:19][S@@:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])([CH2:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:10][F:11].[B-].[Na+]>CO>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@:9]([NH:19][S@@:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])([CH2:12][C@H:13]([OH:18])[C:14]([F:17])([F:15])[F:16])[CH2:10][F:11]

Participants

4

Reactant 2

HCID 22959485VertellusHCID 86732223HCID 86732223, compound

Product 1

HCID 86732222HCID 86732222, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cooled (−15° C.) solution of (R)-N-((S)-2-(2,3-difluorophenyl)-1,5,5,5-tetrafluoro-4-oxopentan-2-yl)-2-methylpropane-2-sulfinamide (5.0 g, 12.84 mmol) in MeOH (20 mL) was added sodium borohydrate (0.729 g, 19.26 mmol). The resulting mixture was stirred at this temperature for 10 min. LCMS indicated reaction went to completion. The mixture was quenched with saturated NaHCO3, diluted with water and extracted with EtOAc (2×). The combined organics were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated and the resulted residue was recrystallized in dichloromethane to afford (R)-N-((2S,4S)-2-(2,3-difluorophenyl)-1,5,5,5-tetrafluoro-4-hydroxypentan-2-yl)-2-methylpropane-2-sulfinamide (2.49 g, 6.36 mmol, 49.5% yield) as white solid. The filtrate was the undesired diastereomers and no further purification was carried out. MS m/z=392.1 [M+H]+. Calculated for C15H19F6NO2S: 391.4

Workup

  1. customreaction
  2. customThe mixture was quenched with saturated NaHCO3
  3. additiondiluted with water
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe resulted residue was recrystallized in dichloromethane

Sources & evidence

ORD record
ord-831ba7e906c84caa963cf45367673cf1
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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