Water → tert-Butyl 4-(pyrrolidin-1-yl)-3,6-dihydropyridine-1(2H)-carboxylate

HRID 2388691Notes

Reaction equation

HRID 2388691 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:12]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.O>C1(C)C=CC=CC=1>[N:26]1([C:22]2[CH2:23][CH2:24][N:19]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:20][CH:21]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 31268PyrrolidineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 1514431tert-Butyl 4-(pyrrolidin-1-yl)-3,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Catalytic amounts of p-toluenesulfonic acid (0.47 g, 0.27 mmol) were added to a solution of N-Boc-4-piperidone (5 g, 25.12 mmol) and pyrrolidine (1.96 g, 27.63 mmol) in toluene (100 ml) and the mixture was stirred under reflux for 2 hours, using a water separator. The solution formed was concentrated to dryness in vacuo and the residue obtained was employed directly in the next stage.

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe solution formed
  3. concentrationwas concentrated to dryness in vacuo
  4. customthe residue obtained

Sources & evidence

ORD record
ord-f8793c6a200b4d9e8ab6297b691e3bdf
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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