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Methanol → 3-{2-[1-(Tert-butoxycarbonyl)-4-piperidinyl]ethyl]benzoic acid

HRID 2074240
Notes
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Reaction equation

HRID 2074240 reaction equation
[OH-].[Na+].C1COCC1.CO.C[O:11][C:12]([C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)[CH:17]=[CH:18][CH:19]=1)=[O:13]>CCOC(C)=O>[C:31]([O:30][C:28]([N:25]1[CH2:26][CH2:27][CH:22]([CH2:21][CH2:20][C:16]2[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=2)[C:12]([OH:13])=[O:11])[CH2:23][CH2:24]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57507758Tert-butyl 4-{2-[3-(methoxycarbonyl)phenyl]ethyl}-1-piperidinecarboxylate

Product 1

HCID 574218263-{2-[1-(Tert-butoxycarbonyl)-4-piperidinyl]ethyl]benzoic acidYield 99.8%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
60 °C

Procedure

Aqueous 1 M sodium hydroxide solution (196 ml) was added to a THF (200 ml)/methanol (50 ml) mixed solution of tert-butyl 4-{2-[3-(methoxycarbonyl)phenyl]ethyl}-1-piperidinecarboxylate (45.4 g), followed by stirring at 60° C. for 2 hours. The organic solvent was evaporated under reduced pressure, and under ice cooling, 0.5 M hydrochloric acid (400 ml) was added to the residue. The reaction liquid was diluted with EtOAc, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 3-{2-[1-(tert-butoxycarbonyl)-4-piperidinyl]ethyl}benzoic acid (43.5 g) was obtained.

Workup

  1. customThe organic solvent was evaporated under reduced pressure
  2. additionunder ice cooling, 0.5 M hydrochloric acid (400 ml) was added to the residue
  3. customThe reaction liquid
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7fd5764bb5d74b3687e60ca3d54310ad
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07919494B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes