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

HRID 1713151Notes

Reaction equation

HRID 1713151 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.CC1C=CC(S(O)(=O)=O)=CC=1>C1CCCCC1>[N:15]1([C:11]2[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH:12]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 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 8078CyclohexaneSolvent

Procedure

A mixture of Boc-4-piperidone (5.5 g, 27.6 mmol), pyrrolidine (2.42 ml, 29 mmol) and PTSA (30 mg) in cyclohexane (30 mL) is refluxed overnight with a Dean-Stark trap to remove water. The mixture is cooled to rt and the solvent is removed in vacuo and the thick oil obtained is used in the next step without further purification.

Workup

  1. temperatureis refluxed overnight with a Dean-Stark trap
  2. customto remove water
  3. customthe solvent is removed in vacuo
  4. customthe thick oil obtained
  5. customis used in the next step without further purification

Sources & evidence

ORD record
ord-8461e3bc36e74507a0a14c9657d030b7
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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