4-Piperidinecarboxylic acid → Tert-butyl Piperidine-4-carboxylate

HRID 1419662Notes

Reaction equation

HRID 1419662 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.[C:10]1([CH3:20])[CH:15]=CC(S(O)(=O)=O)=C[CH:11]=1>C(O)(C)(C)C>[C:10]([O:8][C:7]([CH:4]1[CH2:5][CH2:6][NH:1][CH2:2][CH2:3]1)=[O:9])([CH3:20])([CH3:15])[CH3:11]

Participants

4

Reactant 2

HCID 37734-Piperidinecarboxylic acidHCID 6101p-Toluenesulfonic acid

Product 1

HCID 1512676Tert-butyl Piperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

12.9 g of 4-piperidine carboxylic acid is completely dissolved in 35 ml of t-butyl alcohol (R1OH) and refluxed for 10 hrs. in the presence of 3.8 g of para-toluene sulfonic acid. After being cooled to room temperature, the resulting reaction is washed three times with 20 ml of saturated NaHCO3 and then, once with 25 ml of brine water and dried over MgSO4 to give piperidine-4-carboxylic acid t-butyl ester.

Workup

  1. temperaturerefluxed for 10 hrs
  2. customthe resulting reaction
  3. washis washed three times with 20 ml of saturated NaHCO3
  4. dry with materialonce with 25 ml of brine water and dried over MgSO4

Sources & evidence

ORD record
ord-ed1471d5afe44baea4a403882ceaa98e
Source dataset
uspto-grants-1999_03
Patent number
US05888698

Reaction notes

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