Pyrrolidine → HCID 69018303, compound

HRID 1782035Notes

Reaction equation

HRID 1782035 reaction equation
C([C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[C:7]([O:15]C)[CH:6]=1)(C)(C)C.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.[Al+3].[Cl-].[Cl-].[Cl-]>CN(C=O)C.C1(C)C(C)=CC=CC=1>[N:17]1([S:11]([C:8]2[CH:9]=[CH:10][CH:5]=[CH:6][C:7]=2[OH:15])(=[O:12])=[O:13])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 6451240Aluminum(III) ChlorideHCID 591803954-(1,1-Dimethylethyl)-2-methoxybenzenesulfonyl chloride

Product 1

HCID 69018303HCID 69018303, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7237O-XyleneSolvent

Procedure

To a solution of 4-tert-butyl-2-methoxybenzenesulfonyl chloride (258 mg, 0.99 mmol) in DMF (6 ml) was added pyrrolidine (70 mg, 0.99 mmol) and the solution was stirred at ambient temperature for 30 minutes, and concentrated in vacuo. The residue was dissolved in xylene (10 ml) and then added to mixture of AlCl3 (525 mg, 3.39 mmol) in xylene (5 ml). The resulting mixture was stirred for 18 h at 70° C. After colling the mixture was poured into stirred ice-cold water, and extracted with ether (2×30 ml). The ether layer was dried over sodium sulfate, filtered and concentrated to give 120 mg of subtitle compound.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in xylene (10 ml)
  3. stirringThe resulting mixture was stirred for 18 h at 70° C
  4. additionwas poured
  5. stirringinto stirred ice-cold water
  6. extractionextracted with ether (2×30 ml)
  7. dry with materialThe ether layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-568c9d6a32e34e1fa7c3768c361c2f53
Source dataset
uspto-grants-2009_03
Patent number
US07498338B2

Reaction notes

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