Sodium Hydroxide → 1-(2-Phenylethyl)pyrrolidin-2-one

HRID 521742Notes

Reaction equation

HRID 521742 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6].[OH-].[Na+]>C(Cl)Cl.O.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]>[CH2:8]([N:7]1[CH2:2][CH2:3][CH2:4][C:5]1=[O:6])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 51423824-chloro-N-(2-phenylethyl)butanamide

Product 1

HCID 7469811-(2-Phenylethyl)pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 21908982Water methylene chlorideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of HJC-1-48 (4.2 g, 18.6 mmol) in DCM/H2O (20 mL/8 mL) was added (n-Bu)4NBr (0.3 g, 0.9 mmol) and NaOH (3.7 g, 93.0 mmol). The resulting mixture was stirred at 100° C. for 7 h. The mixture was partitioned between EtOAc (200 mL) and H2O (10 mL). The organic layer was separated and washed with brine (20 mL), dried over anhydrous Na2SO4, filtered and concentrated to give an oil residue. This residue was purified with silica gel column (Hexane/EtOAc=1/1 to 1/2) to obtain HJC-1-53 (4.2 g, 93%) as a pale yellow oil. 1H NMR (600 MHz, CDCl3) δ 7.26-7.30 (m, 2H), 7.18-7.22 (m, 3H), 3.53 (t, 2H, J=7.8 Hz), 3.25 (t, 2H, J=7.2 Hz), 2.84 (t, 2H, J=7.8 Hz), 2.34 (t, 2H, J=7.8 Hz), 1.92-1.97 (m, 2H).

Workup

  1. customThe mixture was partitioned between EtOAc (200 mL) and H2O (10 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (20 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil residue
  8. customThis residue was purified with silica gel column (Hexane/EtOAc=1/1 to 1/2)
  9. customto obtain HJC-1-53 (4.2 g, 93%) as a pale yellow oil

Sources & evidence

ORD record
ord-104c395a0bdb497a844088336bf10a0a
Source dataset
uspto-grants-2016_05
Patent number
US09328125B2

Reaction notes

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