Methanesulfonyl chloride → tert-butyl 4-(1-methyl-1H-imidazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate

HRID 1910393ノート

反応式

HRID 1910393 の反応式
O[C:2]1([C:15]2[N:16]([CH3:20])[CH:17]=[CH:18][N:19]=2)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.CS(Cl)(=O)=O>C(Cl)Cl>[CH3:20][N:16]1[CH:17]=[CH:18][N:19]=[C:15]1[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH:3]=1

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 68570244tert-butyl 4-hydroxy-4-(1-methyl-1H-imidazol-2-yl)piperidine-1-carboxylate

生成物 1

HCID 68598207tert-butyl 4-(1-methyl-1H-imidazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate収率 53.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of tert-butyl 4-hydroxy-4-(1-methyl-1H-imidazol-2-yl)piperidine-1-carboxylate (800 mg) in CH2Cl2 (8 ml) was added methanesulfonyl chloride (0.44 ml) and TEA (1.6 ml) under ice bath cooling, and the mixture was stirred at room temperature for 4 hours. The reaction was quenched with aq. NaHCO2 solution and extracted with EtOAc. The organic phase was washed with brine and dried over MgSO4. Solvent was removed in vacuo, and the residue was purified by silica gel column (CHCl3:MeOH=95:5 to 90:10) to give tert-butyl 4-(1-methyl-1H-imidazol-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (398 mg) as a colorless oil.

後処理

  1. temperaturecooling
  2. customThe reaction was quenched with aq. NaHCO2 solution
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. customSolvent was removed in vacuo
  7. customthe residue was purified by silica gel column (CHCl3:MeOH=95:5 to 90:10)

出典と根拠

ORDレコード
ord-6e885f3717824be197f7b4535daa7f8a
出典データセット
uspto-grants-2013_12
特許番号
US08603975B2

反応ノート

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