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methyl 4-(tert-butyl)-2-(1-Boc-piperidin-4-yloxy)benzoate → 2-(N-Boc-piperidine-4-yloxy)-4-(tert-butyl)benzoic acid

HRID 1445456
Notes
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Reaction equation

HRID 1445456 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=[CH:21][C:16]=2[C:17]([O:19]C)=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=[CH:21][C:16]=2[C:17]([OH:19])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 68532357methyl 4-(tert-butyl)-2-(1-Boc-piperidin-4-yloxy)benzoate

Product 1

HCID 685305052-(N-Boc-piperidine-4-yloxy)-4-(tert-butyl)benzoic acidYield 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

In a 50 ml RBF was suspended methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-tert-butylbenzoate (2.4 g, 6.1 mmol) in 25 ml of 3:1 THF:water to give a light emulsion, then was added solid LiOH monohydrate (567 mg, 13.5 mmol), the flask was fitted with a reflux condenser, and the mixture was heated at 50° C. with stirring for 16 h. The mixture was diluted with 75 ml water and washed twice with diethyl ether. The aqueous layer was acidified to about pH 2 with 1 N NaHSO4, and the resulting slurry extracted twice with 100 ml portions of EtOAc. The combined EtOAc layers were washed with brine, dried, then concentrated in vacuo to afford 2.1 g (91%) of the title acid as a brittle white foam.

Workup

  1. customthe flask was fitted with a reflux condenser
  2. washwashed twice with diethyl ether
  3. extractionthe resulting slurry extracted twice with 100 ml portions of EtOAc
  4. washThe combined EtOAc layers were washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff9417e5950043d8a84ecf34d20bf9c1
Source dataset
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07666866B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes