Hydrochloric Acid → HCID 59428347, compound

HRID 503930Notes

Reaction equation

HRID 503930 reaction equation
Cl.C(OC([N:9]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)(=[O:22])=[O:21])=[CH:16][C:15]=2[CH3:31])[CH2:10]1)=O)(C)(C)C.[OH-].[Na+]>O1CCOCC1>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([C:17]2[CH:18]=[CH:19][C:14]([CH:11]3[CH2:12][CH2:13][NH:9][CH2:10]3)=[C:15]([CH3:31])[CH:16]=2)(=[O:22])=[O:21])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66877158HCID 66877158, compound

Product 1

HCID 59428347HCID 59428347, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of HCl (4.0 M in 1,4-dioxane, 3.4 mL) was added to a solution of 3-[4-(4-methoxy-benzenesulfonyl)-2-methyl-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.845 g, 1.958 mmol) in 1,4-dioxane (2 mL) and the reaction mixture was stirred for 3 hours at room temperature. A solution of NaOH (2.0 M) was added and the mixture was extracted with DCM. 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 (DCM/MeOH/NH4OH) to give 0.650 g of 3-[4-(4-methoxy-benzenesulfonyl)-2-methyl-phenyl]-pyrrolidine as a white foam: MS (M+H)=332.

Workup

  1. extractionthe mixture was extracted with DCM
  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 (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-16c8b1ecee61453ca2e2bbbe18c69288
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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