2,2,6,6-Tetramethylpiperidine → HCID 23510473, compound

HRID 1883211Notes

Reaction equation

HRID 1883211 reaction equation
CC1(C)CCCC(C)(C)N1.[Li]CCCC.[C:16]1([S:22]([N:25]2[CH:29]=[CH:28][CH:27]=[CH:26]2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:30][C:31]1[N:36]=[C:35]([CH:37]=[O:38])[CH:34]=[CH:33][CH:32]=1>C1COCC1.CCCCCC.O>[C:16]1([S:22]([N:25]2[CH:26]=[CH:27][CH:28]=[C:29]2[CH:37]([C:35]2[CH:34]=[CH:33][CH:32]=[C:31]([CH3:30])[N:36]=2)[OH:38])(=[O:24])=[O:23])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 130352,2,6,6-TetramethylpiperidineHCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 1401461-PhenylsulfonylpyrroleHCID 178418339Butyllithium

Product 1

HCID 23510473HCID 23510473, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

Under nitrogen atmosphere, a solution of 2,2,6,6-tetramethyl-piperidine (5.00 mL) in THF (120 mL) was cooled to −78° C., and thereto was added dropwise a 1.6N solution of BuLi in hexane (18.5 mL), and the mixture was stirred at room temperature for 30 minutes. The mixture was cooled again to −78° C., and thereto was added a solution of N-benzenesulfonylpyrrole (5.58 g) in THF (25 mL). The mixture was stirred for 30 minutes, and thereto was added a solution of 6-methyl-pyridine-2-aldehyde (3.94 g) in THF (20 mL), and the mixture was stirred at −78° C. for 2 hours. Water was added to the mixture, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with a saturated brine and dried over MgSO4. The solvent was evaporated under reduced pressure, and the precipitated solid was suspended in a mixed solvent of hexane/ethyl acetate=5/1, and collected by filtration to give [1-(phenylsulfonyl)-1H-pyrrol-2-yl](6-methylpyridin-2-yl)methanol (6.78 g, 77%).

Workup

  1. temperatureThe mixture was cooled again to −78° C.
  2. stirringThe mixture was stirred for 30 minutes
  3. stirringthe mixture was stirred at −78° C. for 2 hours
  4. extractionthe mixture was extracted twice with ethyl acetate
  5. washThe organic layer was washed with a saturated brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated under reduced pressure
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-1e6c771fab4d4f408cea4b6b389d8822
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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