m-Chloroperbenzoic acid → 3-[4-(2-Cyano-benzenesulfonyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 503936Notes

Reaction equation

HRID 503936 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]#[N:28])=[O:20])=[CH:15][C:14]=2[O:29][CH3:30])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:39])C=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]#[N:28])(=[O:39])=[O:20])=[CH:15][C:14]=2[O:29][CH3:30])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 668771343-[4-(2-Cyano-benzenesulfinyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 594283263-[4-(2-Cyano-benzenesulfonyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl esterYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 3-[4-(2-cyano-benzenesulfinyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.135 mg, 0.3165 mmol) dissolved in DCM (5 mL) was added m-CPBA (0.115 mg, 0.9495 mmol), and the mixture was stirred at room temperature for 6 hours. DCM was added and the resulting mixture was washed with sodium thiosulfate (10% aqueous solution), NaHCO3 (saturated aqueous solution), water, and brine. The organic phase was then dried over Na2SO4, filtered, and evaporated under reduced pressure. The resulting crude material was purified via flash chromatography (hexane/EtOAc, 1/1) to give 0.125 g (89% yield) of 3-[4-(2-cyano-benzenesulfonyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a clear oil.

Workup

  1. washthe resulting mixture was washed with sodium thiosulfate (10% aqueous solution), NaHCO3 (saturated aqueous solution), water, and brine
  2. dry with materialThe organic phase was then dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe resulting crude material was purified via flash chromatography (hexane/EtOAc, 1/1)

Sources & evidence

ORD record
ord-4d1a98fad4db44fc8870ba135082dd10
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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