Water → 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(2-fluoroethoxy)benzoic Acid

HRID 1787932Notes

Reaction equation

HRID 1787932 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]([O:25][CH2:26][CH2:27][F:28])[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].O[Li].O.O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([O:25][CH2:26][CH2:27][F:28])[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]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86610261Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(2-fluoroethoxy)benzoate

Product 1

HCID 866102622-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(2-fluoroethoxy)benzoic AcidYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using a procedure similar to that of Example 6-E, methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(2-fluoroethoxy)benzoate (7.28 g) is hydrolyzed using LiOH.H2O (1.78 g, 2.2 equivalents), water (20 mL) and THF (60 mL) at 60-65° C. to afford the acid (2.76 g, 40%).

Workup

  1. customat 60-65° C.

Sources & evidence

ORD record
ord-648d187d3a16427b93e0cce86473ba35
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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