Potassium hydroxy sulfite → 3-[4-(2-Cyano-benzenesulfinyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 503935Notes

Reaction equation

HRID 503935 reaction equation
[OH:1]OS([O-])=O.[K+].[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]#[N:33])=[CH:21][C:20]=2[O:34][CH3:35])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>O.CO.C(#N)C>[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]#[N:33])=[O:1])=[CH:21][C:20]=2[O:34][CH3:35])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 594284293-[4-(2-Cyano-phenylsulfanyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A solution of OXONE™ (0.470 g, 0.7636 mmol) in water (5 mL) was added to a solution of 3-[4-(2-cyano-phenylsulfanyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.209 g, 0.5091 mmol) in a mixture of MeOH (5 mL) and acetonitrile (5 mL). The reaction mixture was stirred at room temperature for 3 hours, then water was added and the mixture was extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The resulting crude material was purified via flash chromatography (hexane/EtOAc, 7/3) to give 0.215 g of 3-[4-(2-cyano-benzenesulfinyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (not shown in Scheme O) as a clear oil.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe resulting crude material was purified via flash chromatography (hexane/EtOAc, 7/3)

Sources & evidence

ORD record
ord-d3097b7aa9a34fc6928048ea4c2cf557
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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