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

HRID 2362777ノート

反応式

HRID 2362777 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 22350042dichloromethane N,N-dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ebdb94662a104b3695f30cdd3227d7aa
出典データセット
uspto-grants-2014_04
特許番号
US08691846B2

反応ノート

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