Hydrogen Peroxide → HCID 90044658, compound

HRID 1050240Notes

Reaction equation

HRID 1050240 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:12][CH:13]=2)=[CH:4][CH:3]=1.[OH-:18].[Na+].OO>C1COCC1.[O-]S([O-])(=S)=O.[Na+].[Na+].CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:12][CH:13]2[OH:18])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 90044660HCID 90044660, compound

Product 1

HCID 90044658HCID 90044658, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

4-(4-chlorophenyl)-1-(methylsulfonyl)-1,2,3,6-tetrahydropyridine (654 mg, 2.407 mmol) was dissolved in THF (4.81 mL). Borane-THF complex (2.407 mL, 2.407 mmol) was added dropwise via syringe and the reaction was stirred 72 h at rt. Then sodium hydroxide (1.5 mL, 4.50 mmol) and hydrogen peroxide (1.2 mL, 11.75 mmol, 30% solution) were added. The reaction was stirred 2 h at rt, then diluted with saturated Na2S2O3 and EtOAc. The aqueous phase was extracted with EtOAc (×2) and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by column chromatography on a Biotage™ 25 g column by eluting with 20% to 100% EtOAc:Hexane to provide the desired product. LC-MS: calculated for C12H16ClNO3S 289.05 observed m/e: 289.92 (M+H)+ (Rt 1.35/4 min).

Workup

  1. additionBorane-THF complex (2.407 mL, 2.407 mmol) was added dropwise via syringe
  2. stirringThe reaction was stirred 2 h at rt
  3. extractionThe aqueous phase was extracted with EtOAc (×2)
  4. washthe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by column chromatography on a Biotage™ 25 g column
  9. washby eluting with 20% to 100% EtOAc

Sources & evidence

ORD record
ord-686ac61c3361401c867909e7dcb20458
Source dataset
uspto-grants-2016_07
Patent number
US09382243B2

Reaction notes

Loading…