Hydrochloric Acid → Tert-Butyl 4-[2-(4-carboxy-3-fluorophenoxymethyl)pyridin-5-yl]piperidine-1-carboxylate

HRID 42148Notes

Reaction equation

HRID 42148 reaction equation
C([O:3][C:4]([C:6]1[CH:32]=[CH:31][C:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)=[CH:14][N:13]=2)=[CH:8][C:7]=1[F:33])=[O:5])C.O.[OH-].[Li+].Cl>C(O)C.O>[C:4]([C:6]1[CH:32]=[CH:31][C:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:20][CH2:19]3)=[CH:14][N:13]=2)=[CH:8][C:7]=1[F:33])([OH:5])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67083233Tert-butyl 4-[2-(4-ethoxycarbonyl-3-fluorophenoxymethyl)pyridin-5-yl]piperidine-1-carboxylate

Product 1

HCID 67083327Tert-Butyl 4-[2-(4-carboxy-3-fluorophenoxymethyl)pyridin-5-yl]piperidine-1-carboxylateYield 101.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of tert-butyl 4-[2-(4-ethoxycarbonyl-3-fluorophenoxymethyl)pyridin-5-yl]piperidine-1-carboxylate (Example 9) (60 mg, 0.131 mmol) in ethanol (0.9 mL)-water (0.2 mL) was added lithium hydroxide monohydrate (16 mg, 0.393 mmol). The mixture was stirred at room temperature overnight, diluted with water, neutralized by the addition of 1N hydrochloric acid and then extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound as a white crystal (57 mg, quantitative yield).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7de12f7c05345048c54f31182592ba7
Source dataset
uspto-grants-2013_09
Patent number
US08536176B2

Reaction notes

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