Rolziracetam → 5-[4-(4-Fluoro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one

HRID 478873Notes

Reaction equation

HRID 478873 reaction equation
[CH2:1]1[CH:8]2[N:4]([C:5](=[O:9])[CH2:6][CH2:7]2)[C:3](=[O:10])[CH2:2]1.[F:11][C:12]1[CH:20]=[CH:19][C:15]([CH2:16][Mg]Cl)=[CH:14][CH:13]=1>>[F:11][C:12]1[CH:20]=[CH:19][C:15]([CH2:16][C:5](=[O:9])[CH2:6][CH2:7][CH:8]2[NH:4][C:3](=[O:10])[CH2:2][CH2:1]2)=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 71893RolziracetamHCID 178505759HCID 178505759, compound

Product 1

HCID 227125185-[4-(4-Fluoro-phenyl)-3-oxo-butyl]-pyrrolidin-2-oneYield 104.9%

Procedure

Following the procedure described for Preparation 8, Step A, tetrahydro-pyrrolizine-3,5-dione (1.41 g, 10.1 mmol) was reacted with 4-fluorobenzylmagnesium chloride (0.25M in Et2O, 50 mL, 12.5 mmol) over 5 h. Purification by medium pressure chromatography (2% MeOH in CH2Cl2) provided 5-[4-(4-fluoro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one (2.64 g). 1H (CDCl3) δ7.18 (m, 2H), 7.03 (m, 2H), 6.34 (m, 1H), 3.70 (s, 2H), 3.62 (m, 1H), 2.54 (t, 2H), 2.34-2.15 (m, 3H), 1.82-1.61 (m, 3H).

Workup

  1. customPurification by medium pressure chromatography (2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-9398ef0e6fa345b2aee10ead8608498d
Source dataset
uspto-grants-2003_11
Patent number
US06642266B2

Reaction notes

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