Nipecotic Acid → 1-(Butylsulfonyl)piperidine-3-carboxylic acid

HRID 1931290Notes

Reaction equation

HRID 1931290 reaction equation
[OH-].[Na+].[NH:3]1[CH2:11][CH2:10][CH2:9][CH:5]([C:6]([OH:8])=[O:7])[CH2:4]1.[CH2:12]([S:16](Cl)(=[O:18])=[O:17])[CH2:13][CH2:14][CH3:15]>>[CH2:12]([S:16]([N:3]1[CH2:11][CH2:10][CH2:9][CH:5]([C:6]([OH:8])=[O:7])[CH2:4]1)(=[O:18])=[O:17])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 4498Nipecotic AcidHCID 14798Sodium HydroxideHCID 754301-Butanesulfonyl chloride

Product 1

HCID 162282211-(Butylsulfonyl)piperidine-3-carboxylic acid

Procedure

1N-sodium hydroxide aqueous solution (4.1 mL) was added to nipecotic acid (500 mg, 3.87 mmol), and, under ice-cooling, butanesulfonylchloride (0.98 mL, 7.74 mmol) was added dropwise. The mixture was raised to room temperature, and stirred for 15 hours. The reaction mixture was then extracted with chloroform. The organic layer was collected, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was then purified using silica gel column chromatography to obtain the target (354 mg, 37%).

Workup

  1. temperatureunder ice-cooling
  2. extractionThe reaction mixture was then extracted with chloroform
  3. customThe organic layer was collected
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was then purified
  7. customto obtain the target (354 mg, 37%)

Sources & evidence

ORD record
ord-93657549469a43839699e61e85c55d82
Source dataset
uspto-grants-2012_05
Patent number
US08188280B2

Reaction notes

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