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Sodium Hydroxide → 3-(3-(N-Boc-piperidin-4-yl)-propoxy)-phenylacetic acid

HRID 2108730
Notes
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Reaction equation

HRID 2108730 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:19]=[C:20]([CH2:24][C:25]([O:27]C)=[O:26])[CH:21]=[CH:22][CH:23]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+]>CO>[C:1]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:19]=[C:20]([CH2:24][C:25]([OH:27])=[O:26])[CH:21]=[CH:22][CH:23]=2)[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21071299Methyl 3-(3-(N-Boc-piperidin-4-yl)-propoxy)-phenylacetate

Product 1

HCID 210712953-(3-(N-Boc-piperidin-4-yl)-propoxy)-phenylacetic acidYield 61.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 3-(3-(N-Boc-piperidin-4-yl)-propoxy)-phenylacetate (0.5 g, 1.3 mmol) was dissolved in methanol and 2N NaOH (3 mL) added. The reaction was stirred at 60° C. for 2 hours then the solution was adjusted to pH 6.5. The product was extracted into ethyl acetate, and the organic phase was dried by MgSO4. The solvent was evaporated to afford 3-(3-(N-Boc-piperidin-4-yl)-propoxy)-phenylacetic acid (0.30 g). 1H NMR (500 MHz, CDCl3) 1.02 (m, 2H), 1.25 (m, 2H), 1.55 (m, 2H), 1.65 (m, 2H), 2.57 (m, 2H), 3.33 (m, 1H), 3.75 (s, 2H), 3.95 (m, 2H), 6.63 (m, 3H), 6.98 (m, 1H).

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. dry with materialthe organic phase was dried by MgSO4
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9531105339d84a769d3d84f1b57cd9c5
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07514448B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes