5-(3,5-Di-tert-butylphenyl)-2-methyl-1-(piperidin-1-ylsulfonyl)-1H-pyrrole-3-carboxylic acid → 1-((2-(3,5-Di-tert-butylphenyl)-5-methyl-1H-pyrrol-1-yl)sulfonyl)piperidine

HRID 1844716Notes

Reaction equation

HRID 1844716 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:15]2[N:19]([S:20]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)(=[O:22])=[O:21])[C:18]([CH3:29])=[C:17](C(O)=O)[CH:16]=2)[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)(C(F)(F)F)=O>[C:1]([C:5]1[CH:6]=[C:7]([C:15]2[N:19]([S:20]([N:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)(=[O:21])=[O:22])[C:18]([CH3:29])=[CH:17][CH:16]=2)[CH:8]=[C:9]([C:11]([CH3:13])([CH3:14])[CH3:12])[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 708727905-(3,5-Di-tert-butylphenyl)-2-methyl-1-(piperidin-1-ylsulfonyl)-1H-pyrrole-3-carboxylic acid

Product 1

HCID 867191321-((2-(3,5-Di-tert-butylphenyl)-5-methyl-1H-pyrrol-1-yl)sulfonyl)piperidineYield 41.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of compound 4d (700 mg, 1.5 mmol) in TFA (5 mL) was heated to 100° C. for 30 min, evaporated and redissolved in EA, washed with aq. NaHCO3 (3×50 mL) and brine, dried with Na2SO4, concentrated and purified by CC (PE/EA=1/0 to 7/1) to get compound 4e (260 mg, 41%).

Workup

  1. customevaporated
  2. dissolutionredissolved in EA
  3. washwashed with aq. NaHCO3 (3×50 mL) and brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. custompurified by CC (PE/EA=1/0 to 7/1)

Sources & evidence

ORD record
ord-b324159ea2f6480a80c006aadfcd66cf
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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