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

HRID 1910393Notes

Reaction equation

HRID 1910393 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-6e885f3717824be197f7b4535daa7f8a
Source dataset
uspto-grants-2013_12
Patent number
US08603975B2

Reaction notes

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