Rolziracetam → 5-(3-Oxo-4-phenyl-butyl)-pyrrolidin-2-one

HRID 352572

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.[CH2:11]([Mg]Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[O:9]=[C:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][CH2:7][CH:8]1[NH:4][C:3](=[O:10])[CH2:2][CH2:1]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tetrahydro-pyrrolizine-3,5-dione (5 g, 36 mmol) in CH2Cl2 (320 mL) at 0° C. was added benzyl magnesium chloride (1M solution in THF, 39 mL, 39 mmol) dropwise. The solution was stirred at 0° C. for 3 h and was quenched with saturated aqueous ammonium chloride. After warming to room temperature, the aqueous solution was extracted with CH2Cl2 (3×). The combined organic extracts were dried (MgSO4), filtered and concentrated. The residue was purified by medium pressure chromatography eluting with a solvent gradient (1% MeOH in CH2Cl2to 2% MeOH in CH2Cl2) to yield 5.9021 g of 5-(3-oxo-4-phenyl-butyl)-pyrrolidin-2-one. 1H NMR (CDCl3) δ7.35-7.18 (m, 5H), 3.69 (s, 2H), 3.56 (m, 1H), 2.50 (t, 2H), 2.27 (m, 2H), 2.15 (m, 1H), 1.73 (m, 2H), 1.61 (m, 1H).

Workup

customwas quenched with saturated aqueous ammonium chloride
temperatureAfter warming to room temperature
extractionthe aqueous solution was extracted with CH2Cl2 (3×)
dry with materialThe combined organic extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by medium pressure chromatography
washeluting with a solvent gradient (1% MeOH in CH2Cl2to 2% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-722a73397ead4923b5bab1758844c0e8
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06747054B2

Linked notes

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