(S)-N-((S)-(4-formylphenyl)(3-(trifluoromethyl)pyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide → (S)-N-((1S)-(4-(1-hydroxyethyl)phenyl)(3-(trifluoromethyl)pyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide

HRID 509335Notes

Reaction equation

HRID 509335 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([C:17]2[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:20]=[CH:19][N:18]=2)[NH:10][S@:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])=[CH:5][CH:4]=1)=[O:2].[CH3:27][Mg]Br>C1COCC1>[OH:2][CH:1]([C:3]1[CH:4]=[CH:5][C:6]([C@@H:9]([C:17]2[C:22]([C:23]([F:25])([F:26])[F:24])=[CH:21][CH:20]=[CH:19][N:18]=2)[NH:10][S@:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[O:12])=[CH:7][CH:8]=1)[CH3:27]

Participants

4

Reactant 2

HCID 86687954(S)-N-((S)-(4-formylphenyl)(3-(trifluoromethyl)pyridin-2-yl)methyl)-2-methylpropane-2-sulfinamideHCID 178418573HCID 178418573, compound

Product 1

HCID 86687955(S)-N-((1S)-(4-(1-hydroxyethyl)phenyl)(3-(trifluoromethyl)pyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)—N—((S)-(4-Formylphenyl)(3-(trifluoromethyl)pyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide (0.200 g, 0.520 mmol) was dissolved in dry THF (30 mL) and cooled in an ice bath. Methylmagnesium bromide (3M in Et2O, 0.50 mL, 1.50 mmol) was added dropwise and the reaction stirred. The resulting mixture was stirred for 1 h and then quenched by addition of saturated aqueous NH4Cl (10 mL). H2O (100 mL) and EtOAc (100 mL) were added, and the phases were mixed and separated. The organic layer was dried with MgSO4 and evaporated to dryness under reduced pressure. Purification using silica chromatography (hexane to EtOAc gradient) gave impure material which was further purified using reverse phase HPLC to give the desired (S)—N-((1 S)-(4-(1-hydroxyethyl)phenyl)(3-(trifluoromethyl)pyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide.

Workup

  1. temperaturecooled in an ice bath
  2. stirringThe resulting mixture was stirred for 1 h
  3. customquenched by addition of saturated aqueous NH4Cl (10 mL)
  4. additionH2O (100 mL) and EtOAc (100 mL) were added
  5. additionthe phases were mixed
  6. customseparated
  7. dry with materialThe organic layer was dried with MgSO4
  8. customevaporated to dryness under reduced pressure
  9. customPurification
  10. customgave impure material which
  11. customwas further purified

Sources & evidence

ORD record
ord-eaa04245bdfc4347972559a20d96a5c6
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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