Nipecotic Acid → 1-((Benzyloxy)carbonyl)piperidine-3-carboxylic acid

HRID 1506125Notes

Reaction equation

HRID 1506125 reaction equation
[NH:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([OH:6])=[O:5])[CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].[OH-].[Na+]>O>[CH2:20]([O:19][C:17]([N:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([OH:6])=[O:5])[CH2:2]1)=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 4498Nipecotic AcidHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 2343391-((Benzyloxy)carbonyl)piperidine-3-carboxylic acidYield 73.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Nipecotic acid (3.93 g, 30.4 mmol) and sodium carbonate (5.10 g, 48.1 mmol) in water (40 mL) was mixed with benzyl chloroformate (5.20 mL, 36.4 mmol) under cooling with ice and stirred at room temperature for one day. After addition of water and 1 M aqueous sodium hydroxide, the reaction mixture was allowed to separate by adding diethyl ether. The aqueous layer was adjusted to pH 1 with concentrated hydrochloric acid and extracted with ethyl acetate. The resulting organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound as a pale yellow oil (5.86 g, yield 73%).

Workup

  1. temperatureunder cooling with ice
  2. customto separate
  3. additionby adding diethyl ether
  4. extractionextracted with ethyl acetate
  5. washThe resulting organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e792ac238710487982a0df1c0b315f66
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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