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

HRID 1910393노트

반응식

HRID 1910393 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6e885f3717824be197f7b4535daa7f8a
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08603975B2

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