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Lithium Hydroxide → 1-[(Benzyloxy)carbonyl]-3-methylpiperidine-3-carboxylic acid

HRID 875609
Notes
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Reaction equation

HRID 875609 reaction equation
[CH3:1][C:2]1([C:18]([O:20]CC)=[O:19])[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1.[Li+].[OH-]>C(O)C>[CH2:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][CH2:7][C:2]([CH3:1])([C:18]([OH:20])=[O:19])[CH2:3]1)=[O:9])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 534862661-Benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate

Product 1

HCID 532493621-[(Benzyloxy)carbonyl]-3-methylpiperidine-3-carboxylic acidYield 93.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
86 °C

Procedure

To 1-benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate (3.0 g, 10.0 mmol) in ethanol (15 mL) was added LiOH (15.0 mL, 30.1 mmol), and the reaction mixture was stirred at 86° C. for 1 hour. The ethanol was removed, and ether (30 mL) was added. The aqueous layer was separated and acidified with saturated potassium hydrogen sulfate to a pH of about 3 to about 4, extracted with ethyl acetate (50 mL), and washed with brine and dried over sodium sulfate. After removal of the solvent, 1-(benzyloxycarbonyl)-3-methylpiperidine-3-carboxylic acid (2.6 g, 92% yield) was isolated as an oil.

Workup

  1. customThe ethanol was removed
  2. additionether (30 mL) was added
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (50 mL)
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customAfter removal of the solvent

Sources & evidence

ORD record
ord-0b43643e63fe45f288239327d6d54c55
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08981085B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes