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

HRID 644168Notes

Reaction equation

HRID 644168 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[O:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.[Li+].[OH-].CO.C1COCC1>CCOC(C)=O>[C:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][CH:12]([O:11][C:5]2[CH:6]=[C:7]([F:10])[CH:8]=[CH:9][C:4]=2[C:3]([OH:25])=[O:2])[CH2:13][CH2:14]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

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 was diluted with EtOAc, washed with satd citric acid, dried over MgSO4, concentrated, and triturated with ether to give the desired product 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-b25a0d8f4e14403d91e7a5fd614469da
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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