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

HRID 1808337Notes

Reaction equation

HRID 1808337 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 for 2 hours under reflux with a water separator. The resulting solution was concentrated to dryness in vacuo and the resulting residue was used directly in the following stage.

Workup

  1. concentrationThe resulting solution was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-03c57132ad9b4cd58d57f36bd767e826
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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