Sodium Hydroxide → 1-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acid

HRID 2287434Notes

Reaction equation

HRID 2287434 reaction equation
C([O:3][C:4](=[O:19])[C:5]1([CH3:18])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)C.[OH-].[Na+]>C1COCC1.C(O)C.OS([O-])(=O)=O.[K+].OS(O)(=O)=O>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][C:5]([CH3:18])([C:4]([OH:19])=[O:3])[CH2:6][CH2:7]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 162182761-tert-Butyl 4-ethyl 4-methylpiperidine-1,4-dicarboxylate

Product 1

HCID 232828481-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acidYield 26.5%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 1118Sulfuric AcidSolventHCID 8028TetrahydrofuranSolventHCID 516920Potassium bisulfateSolvent

Procedure

To a stirring solution of N-tert-butoxycarbonyl-4-methylisonipecotic acid ethyl ester (17.4 mmol, 4.73 g) in THF (50 mL) and ethanol (50 mL) was added 50% NaOH (50 mL) and the mixture heated to reflux overnight. The reaction was diluted with 10% KHSO4 (600 mL) and conc. H2SO4 (5 mL) and extracted with ethyl acetate (2×250 mL). The organic layers were combined, washed with water (500 mL) and brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was triturated with diethyl ether:hexanes and filtered to give 1.12 g of an orange solid. The filtrates were evaporated to give 2.71 g of the title compound as an orange solid.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux overnight
  3. extractionextracted with ethyl acetate (2×250 mL)
  4. washwashed with water (500 mL) and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was triturated with diethyl ether
  8. filtrationhexanes and filtered

Sources & evidence

ORD record
ord-3f40a977c5f840db8a700f25ea84f669
Source dataset
uspto-grants-2000_07
Patent number
US06083949

Reaction notes

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