Diisopropylethylamine → [1-(2-Chloro-benzenesulfonyl)-piperidin-3-yl]-(2-m-tolyl-pyrrolidin-1-yl)-methanone

HRID 220207Notes

Reaction equation

HRID 220207 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([O-:19])=O)[CH2:12]1)(=[O:10])=[O:9].[Li+].[CH3:21][C:22]1[CH:23]=[C:24]([CH:28]2[CH2:32][CH2:31][CH2:30][NH:29]2)[CH:25]=[CH:26][CH:27]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]([N:29]2[CH2:30][CH2:31][CH2:32][CH:28]2[C:24]2[CH:23]=[C:22]([CH3:21])[CH:27]=[CH:26][CH:25]=2)=[O:19])[CH2:12]1)(=[O:9])=[O:10]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 35440982-(3-Methylphenyl)pyrrolidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67131265Lithium 1-(2-chloro-benzenesulfonyl)-piperidine-3-carboxylate

Product 1

HCID 57822305[1-(2-Chloro-benzenesulfonyl)-piperidin-3-yl]-(2-m-tolyl-pyrrolidin-1-yl)-methanoneYield 23.1%

Reagents, catalysts & solvents 2

HCID 22350042dichloromethane N,N-dimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution 0.1 g Lithium 1-(2-chloro-benzenesulfonyl)-piperidine-3-carboxylate (0.32 mmol) in DMF: DCM (3:1) was added 0.047 g 2-(3-methyl phenyl)-pyrrolidine (0.29 mmol) and 0.27 mL DIPEA (1.6 mmol). The mixture was stirred for 10 minutes at room temperature and 0.147 g HATU (0.38 mmol) was added. The mixture was stirred overnight at room temperature, diluted with 15 mL brine and extracted with ethyl acetate (3×10 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to dryness to obtain the crude product which was further purified by column chromatography on silica eluting with 15% ethyl acetate in hexane to yield 0.03 g (20.8%) of the title compound. (MH+) 447.07.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure to dryness
  6. customto obtain the crude product which
  7. customwas further purified by column chromatography on silica eluting with 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-eaaebfd08dca4d62948c694e4235ded4
Source dataset
uspto-grants-2012_06
Patent number
US08202888B2

Reaction notes

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