HCID 23381518, compound → HCID 69968980, compound

HRID 1280726Notes

Reaction equation

HRID 1280726 reaction equation
[F:1][C:2]([F:25])([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:3][N:4]1[CH2:8][CH2:7][C@H:6]([S:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH2:5]1.[OH:26]OS([O-])=O.[K+]>CO>[F:25][C:2]([F:1])([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:3][N:4]1[CH2:8][CH2:7][CH:6]([S:9]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[O:26])[CH2:5]1

Participants

4

Reactant 2

HCID 23381518HCID 23381518, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 69968980HCID 69968980, compoundYield 108.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(3S)-4-[1-(2,2-Difluoro-4-phenyl-butyl)-pyrrolidin-3-ylsulfanyl]-phenol (0.25 g, 0.688 mmol) was dissolved in MeOH (20 ml), cooled to 0° C. and treated with oxone (0.21 g, 0.34 mmol). After 4 hours stirring at 0° C., reaction mixture was quenched with saturated NaHCO3 (65 ml). Aqueous phase was extracted with CH2Cl2 (3 times). Combined organic phases were dried over Na2SO4 and the solvent was evaporated. The residue was chromatographed by MPLC over silica gel (hexane-ethyl acetate, 98:2 to 50:50) to provide (3S,S-oxide R) or (3S, S-oxide S)-4-[1-(2,2-difluoro-4-phenyl-butyl)-pyrrolidine-3-sulfinyl]-phenol (140 mg, first fraction, 54%), MS: m/e=380.4 (M+H+).

Workup

  1. customreaction mixture
  2. customwas quenched with saturated NaHCO3 (65 ml)
  3. extractionAqueous phase was extracted with CH2Cl2 (3 times)
  4. dry with materialCombined organic phases were dried over Na2SO4
  5. customthe solvent was evaporated
  6. customThe residue was chromatographed by MPLC over silica gel (hexane-ethyl acetate, 98:2 to 50:50)

Sources & evidence

ORD record
ord-2a9e21de5fd04d7da99947293c1ca36d
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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