Pyrrolidine → 5-Methanesulfonyl-2-pyrrolidin-1-yl-benzoic acid

HRID 32676Notes

Reaction equation

HRID 32676 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>>[CH3:14][S:11]([C:8]1[CH:9]=[CH:10][C:2]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])(=[O:13])=[O:12]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 23291322-Chloro-5-(methylsulphonyl)benzoic acid

Product 1

HCID 597934895-Methanesulfonyl-2-pyrrolidin-1-yl-benzoic acid

Procedure

A mixture of 163.8 mg (0.7 mmol) 2-Chloro-5-methanesulfonyl-benzoic acid in 2 ml pyrrolidine was heated for 16 h to 100° C. After evaporation of all volatiles the residue was taken up in 2 ml methanol/formic acid 3/1 and subjected to reversed phase HPLC purification eluting with an acetonitrile/water gradient to yield after evaporation of the product fractions 143.4 mg (77%) of the title compound. MS (m/e): 268.1 (MH−, 100%).

Workup

  1. temperaturewas heated for 16 h to 100° C
  2. customAfter evaporation of all volatiles the residue
  3. customsubjected to reversed phase HPLC purification
  4. washeluting with an acetonitrile/water gradient
  5. customto yield
  6. customafter evaporation of the product fractions 143.4 mg (77%) of the title compound

Sources & evidence

ORD record
ord-8e32238ca05049a08a39b00ab9cfb165
Source dataset
uspto-grants-2008_09
Patent number
US07427612B2

Reaction notes

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