Methanol → 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoic acid

HRID 1787892Notes

Reaction equation

HRID 1787892 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]([F:25])[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].[Li+].[OH-].CO.C1COCC1>CCOC(C)=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]([F:25])[CH:22]=[CH:21][C:16]=2[C:17]([OH:19])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 57602502Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoate

Product 1

HCID 576024392-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoic acidYield 76.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoate (3.05 g, 8.64 mmol), 1 M aq LiOH (15 mL, 15 mmol), MeOH (15 mL), and THF (45 mL) was stirred overnight. The reaction mixture was diluted with EtOAc, washed with satd citric acid, dried over MgSO4, concentrated, and triturated with ether to give the acid as a white solid (2.23 g, 76%).

Workup

  1. washwashed with satd citric acid
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customtriturated with ether

Sources & evidence

ORD record
ord-d389d159301e4655a135a97230471e10
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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