Potassium Carbonate → Tert-butyl 4-cyano-4-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidine-1-carboxylate

HRID 2193078ノート

反応式

HRID 2193078 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:14])=[CH:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.[H-].[Na+].[C:17]([C:19]1([CH2:32][CH2:33]OS(C)(=O)=O)[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1)#[N:18].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O.CN(C)C=O>[C:17]([C:19]1([CH2:32][CH2:33][N:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[C:7]([CH3:14])=[CH:8][C:9]2=[O:13])[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:21][CH2:20]1)#[N:18]

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 7615487-Methoxy-4-methylquinolin-2-olHCID 86617989Tert-butyl 4-cyano-4-(2-((methylsulfonyl)oxy)ethyl)piperidine-1-carboxylate

生成物 1

HCID 67540183Tert-butyl 4-cyano-4-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidine-1-carboxylate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To 5 mL of an N,N-dimethylformamide solution containing 0.19 g of 7-methoxy-4-methylquinolin-2(1H)-one, 47 mg of a 60% aqueous sodium hydride solution was added at 50° C., and the mixture was stirred at the same temperature for 40 minutes. Thereto was added dropwise 4 mL of an N,N-dimethylformamide solution containing 0.36 g of tert-butyl 4-cyano-4-(2-((methylsulfonyl)oxy)ethyl)piperidine-1-carboxylate at 50° C., and the mixture was stirred at 50 to 55° C. for 3 hours. Thereto was added 0.27 g of potassium carbonate at the same temperature, and the mixture was further stirred for 3 hours and 10 minutes. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The organic layer was separated, washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by flash silica gel column chromatography [hexane:gradient elution of ethyl acetate=75:25 to 50:50] to obtain 70 mg of a colorless oily substance, tert-butyl 4-cyano-4-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)piperidine-1-carboxylate.

後処理

  1. additionwas added at 50° C.
  2. stirringthe mixture was stirred at 50 to 55° C. for 3 hours
  3. stirringthe mixture was further stirred for 3 hours and 10 minutes
  4. customThe organic layer was separated
  5. washwashed with an aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by flash silica gel column chromatography [hexane:gradient elution of ethyl acetate=75:25 to 50:50]

出典と根拠

ORDレコード
ord-45db995f65fc458aa874e884ab0ce5e2
出典データセット
uspto-grants-2012_12
特許番号
US08329694B2

反応ノート

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