Hydrochloric Acid → 1-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acid

HRID 659608Notes

Reaction equation

HRID 659608 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([OH:9])=[O:8])[CH2:2]1.[C:10]([O-:13])([O-])=[O:11].[K+].[K+].Cl>CCO.O>[C:3]([O:13][C:10]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([OH:9])=[O:8])[CH2:2]1)=[O:11])([CH3:7])([CH3:4])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4498Nipecotic AcidHCID 11430Potassium Carbonate

Product 1

HCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acidYield 249.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A 250-mL 3-necked round-bottomed flask was charged with a solution of piperidine-3-carboxylic acid (4.0 g, 30.39 mmol, 1.00 equiv, 98%) in EtOH (70 mL), tert-butoxycarbonyl (8.2 g, 36.86 mmol, 1.21 equiv, 98%) and K2CO3 (4.3 g, 30.54 mmol, 1.00 equiv, 98%). The resulting mixture was stirred overnight at room temperature overnight. Then, the mixture was diluted with water. The pH was adjusted to 3 with aqueous 10% HCl resulting in a precipitate. The mixture was then filtered to collect solids that were washed with water and dried in a vacuum oven under reduced pressure to afford 1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid as white solid (8.7 g).

Workup

  1. filtrationThe mixture was then filtered
  2. customto collect solids that
  3. washwere washed with water
  4. customdried in a vacuum oven under reduced pressure

Sources & evidence

ORD record
ord-aabf643ea2c149e9aed1f19c733ba272
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

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