HCID 9924295, compound → HCID 69969745, compound

HRID 1280725Notes

Reaction equation

HRID 1280725 reaction equation
[F:1][CH:2]([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:25]OS([O-])=O.[K+]>CO>[F:1][CH:2]([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:25])[CH2:5]1

Participants

4

Reactant 2

HCID 9924295HCID 9924295, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 69969745HCID 69969745, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(2RS,3R)-4-[1-(2-Fluoro-4-phenyl-butyl)-pyrrolidin-3-ylsulfanyl]-phenol (0.56 g, 1.62 mmol) was dissolved in MeOH (50 ml), cooled to 0° C. and treated with oxone (0.5 g, 0.81 mmol). After 4 hours stirring at 0° C., reaction mixture was quenched with saturated NaHCO3 (65 ml). Aqueous phase was extracted with CH2Cl2 (6 times). Combined organic phases were dried over Na2SO4 and the solvent was evaporated. The residue was chromatographed by MPLC over silica gel (CH2Cl2—MeOH, 99:1 then 98:2) then by preparative HPLC (EtOH-heptane, 08:92, detection at 254 nm) to provide (2R,3R, S-oxide R)-4-[1-(2-fluoro-4-phenyl-butyl)-pyrrolidine-3-sulfinyl]-phenol (30 mg, first fraction, 5%), MS: m/e=362.2 (M+H+).

Workup

  1. customreaction mixture
  2. customwas quenched with saturated NaHCO3 (65 ml)
  3. extractionAqueous phase was extracted with CH2Cl2 (6 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 (CH2Cl2—MeOH, 99:1

Sources & evidence

ORD record
ord-b95285b7f9f449efb71a3b5ce80a85ac
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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