Ethyl Acetate → 2-(2-Oxo-3-phenylpiperidin-1-yl)acetic acid

HRID 1667176Notes

Reaction equation

HRID 1667176 reaction equation
[O:1]=[C:2]1[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][N:3]1[CH2:14][C:15]([O:17]CC)=[O:16].[OH-].[Na+].C(OCC)(=O)C>CO>[O:1]=[C:2]1[CH:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][N:3]1[CH2:14][C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67359618HCID 67359618, compound

Product 1

HCID 673587022-(2-Oxo-3-phenylpiperidin-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product from Example 91C (2.7 g, 10.33 mmol) in methanol (10 mL) was added sodium hydroxide (2.0 M) (10.33 ml, 20.66 mmol). After stirring for 30 minutes, thin layer chromatography (100% ethyl acetate) showed complete consumption of the starting material. The reaction was diluted with ethyl acetate (50 mL), washed with 1 N HCl (50 mL) and brine (50 mL), dried over magnesium sulfate, and concentrated to supply the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.41-7.15 (m, 5H), 4.35 (d, J=16.9, 1H), 4.01 (d, J=16.9, 1H), 3.80-3.69 (m, 1H), 3.68-3.51 (m, 1H), 3.44 (dt, J=5.6, 11.3, 2H), 2.31-2.12 (m, 1H), 2.09-1.77 (m, 3H).

Workup

  1. customconsumption of the starting material
  2. additionThe reaction was diluted with ethyl acetate (50 mL)
  3. washwashed with 1 N HCl (50 mL) and brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to supply the title compound

Sources & evidence

ORD record
ord-f5e8bd98b9884407897e6640a9218c20
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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