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

HRID 458984Notes

Reaction equation

HRID 458984 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

Analogous to the procedure described for Example 1A, 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 NMR (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-efcc0c79805a485588f610f72420a0a5
Source dataset
uspto-grants-2007_03
Patent number
US07192979B2

Reaction notes

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