Sodium Hydroxide → 2-Oxo-1-pyrrolidinepropanoic acid

HRID 1453009Notes

Reaction equation

HRID 1453009 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7]CC#N.[OH-:11].[Na+].[O:13]1[CH2:18][CH2:17]OCC1>>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:17][C:18]([OH:13])=[O:11]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 3526242-Oxo-1-pyrrolidinepropionitrile

Product 1

HCID 31466882-Oxo-1-pyrrolidinepropanoic acidYield 49%

Procedure

A solution of 2-oxo-1-pyrrolidinepropionitrile (22.4 g, 16.2 mmol), 15% NaOH solution (40 mL) and dioxane (40 mL) was heated under reflux for 5 h under N2. The reaction mixture was extracted with EtOAc. The aqueous layer was made acidic with 6N HCl amd extracted with CH2Cl2 (5×50 mL). The organic layers were dried over Na2SO4 and concentrated to give the title compound as a cream solid (12.4 g, 49%). 1H NMR (CDCl3): δ 2.04 (m, 2H), 2.42 (t, 2H, J=7.9 Hz), 2.60 (t, 2H, J=6.8 Hz), 3.48 (t, 2H, J=7.2 Hz), 3.59 (t, 2H, J=6.8 Hz), 10.29 (br s, 1H).

Workup

  1. temperatureunder reflux for 5 h under N2
  2. extractionThe reaction mixture was extracted with EtOAc
  3. extractionamd extracted with CH2Cl2 (5×50 mL)
  4. dry with materialThe organic layers were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0a8f590d03804486b41f5bba2124df17
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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