2-Oxo-l-pyrrolidines

Oxopropionic acid 2-Oxo-l -pyrrolidine-propionitrile CH3C(=0)C02H 88.06 138.17 3, 608... 

Pyrrolidone is first reacted with sodium hydride, then with ethyl chloroacetate to give ethyl 2-oxo-l-pyrrolidine acetate. 

A solution of 0.3 mol of ethyl 2-oxo-l-pyrrolidine acetate in 300 ml of methanol, saturated with ammonia at 20° to 30°C, is heated at 40° to 50°C for 5 hours, while continuously introducing ammonia. The reaction mixture is evaporated to dryness and the residue recrystallized from isopropanol. 2-Oxo-1-pyrrolidineacetamide is obtained in a yield of 86%. MP 151.5° to 152.5°C. 

Oxiracetam (4-hydroxy-2-oxo-l-pyrrolidine acetamide) [62613-82-5 unspecified, 68567-97-5 racemate] M 158.2, m 165-168°. This nootropic (Alzheimer) drug is purified by reciystallisation from MeOH or aqueous Mc2CO and dried in vacuo. [NMR, IR Pifferi Pinza Farmaco Ed Sci 32 602 1977, Banfi et al. Farmaco Ed Sci 39 16 1984, Gouilaev Semdng Brain Research Rev 19 180 1994.]... 

Piracetam (2-oxo-l-pyrrolidine acetamide) was given intraperitoneally to rats 30 min before starting hypoxic exposure. In old Wistar rats, 400 mg piracetam per kg body weight x day were added to the food (powdered Altromin R) and drinking water. 

A mixture of ferf-enamide (1 1.0 mmol) and indole derivative (2 1.0 mmol) in acetic acid (1.0 mL) was stirred at room temperature for stipulated time (7-24 h). On completion of the reaction (as monitored by TLC), the reaction mixture was poured into water, and NaHC03 was added to neutralize the acetic acid. The crude product was extracted with CH2CI2 (15 mL X 2) the organic layer was dried with anhydrous Na2S04. On removal of the solvent under reduced pressure, desired product of 2-oxo-l -pyrrolidine 3 was obtained, which was then purified by flash column chromatography using ethyl acetate and petroleum ether as eluents to afford pure product. All the products were characterized by spectral smdies. 

Kenda B, Quesnel Y, Ates A, Michel P, Turet L (2006) 2-Oxo-l-pyrrolidine derivatives and... 

Pyrrol 2-Methoxy-4-methyl-3-phenyl- E6a, 616 (2-OH — 2-OR) Pyrrolidin 2-Oxo-l-(2-phenyl-ethenyl)- XI/2, 570 Quinolin... 

Acety l-( 1 -cyan-1 -phenyl-buty 1)-E13/1, 829 (H - O-OAcyl) Pyrrolidin 3-Acetoxy-4-methyl-2-oxo-l-phenyl- E21c, 2258 [Allyl-N( Ar) - CO - CHX -R + R3SnH]... 

CliHi2N2O, 1,1-Dimethyl-3-phenylpyrazolium-5-oxide, 35B, 161 CliHi2N2O, 3,4-Dimethyl-2,2 -pyrromethen-5(1H)-one, 45B, 208 CliHi2N2OS, 2-Oxo-l-(phenylaminothiocarbonyl)pyrrolidine, 39B, 165 CliHi3CIN2O3, p-Chlorobenzylammonium N-hydroxysuccinimide, 43B, 273 CliHi3CI3N2O, a-2-(2,6-Dichlorophenoxyethyl)imidazolidine hydrochloride, 46B, 207... 

S)-1 -[(2J )-2-ethyl-l-oxo-10-undecenyl]-2-[(2-mcthoxycthoxy)methoxymeLhyl]pyrrolidine is treated with successive portions of dried zinc bromide (4 g/g amide) in CH,C12 solution until around 10 % of the starting... 

Die 1-Aminierung mit O-Diphenylphosphinyl-hydroxylamin und Natriumhydrid in 1-Methyl-2-oxo-pyrrolidin ist sowohl fur wasserlosliche als auch fur wasserunlosliche Imidazole geeignet. Auch hier werden die Produkte iiblicherweise iiber die 1-Benzylidenamino-imidazole ge-reinigt. Auf diese Weise werden 1-Amino-611, l-Amino-4-nitro-611, l-Amino-2-methyl-4-ni(ro-611, l-Amino-2-methyl-61s und l-Amino-2-phenyl-imidazol678 hergestellt. 

In Fallen wie bei 2-(5-Oxo-pyrrolidin-2-yl)-l,3,4-oxadiazolen, wo konventionelle Me-thoden oft versagen oder maBige Ausbeuten liefern, hat sich eine Miscliung aus Phosphor(V)-oxid und Methansulfonsaure bewahrt357. 

Nitromethyl-l-oxo-cycloalkane bzw. 1-Nitromethyl-cycloalkene lassen sich mit Pyrro-lidinen oder (S,)-2-Methoxymethyl-pyrrolidin bzw. -piperidin in Acetonitril bei 20° unter Austausch der Nitro-Gruppe in guten Ausbeuten in 2-(Pyrrolidino-methyl)-l-oxo-cycloalkane3 bzw. l-(Piperidino-methyl)-cycloalkene8 uberfuhren (s.a. S. 378) ... 

Chlor-ethyl)-l,4-diaryl-2-oxo-azetidine reagieren mit Natriumcyanid in Methanol unter Umlagcrung und Bildung von Pyrrolidinen, z.B. trans-1,2-Diphenyl-3-methoxy-carbonyl-pyrrolidin (65%) bzw. trans-3-Methoxycarbonyl-l-(4-methoxy-phenyl)-2-(3-py-ridinyl)-pyrrolidin (52%)3 ... 

Condensation of the pyrrolidine enamine of cyclohexanone with l,l-dicyano-2,2-dimethylcyclopropane proceeds smoothly in refluxing dry xylene and gives the expected adduct in 76% yield. Recrystallisation of the adduct from 95% ethanol, however, gave a 91% yield of a product which no longer contained the pyrrolidine group but whose spectral data clearly showed the presence of a ketone group and an enaminonitrile function. Hydrolysis of this latter product with phosphoric acid/acetic acid gave 5-(2-oxo-4,4-dimethylcyclopentyl)pentanoic acid in 83% yield. 

Ethyl 1 -(2-chloroethyl)-4-oxo-7-(pyrrolidin-1 -yl)-1,4-dihydro-1,8-naphthyri-dine-3-carboxylate (29) gave 4-oxe-7-(pyrrolidin-l-yl)-l-vinyl-1,4-dihydro-... 

Preparation of (S)-[l-(3-hydroxyadamantan-l-yl)-2-oxo-2-pyrrolidin-l-ylethyl]-carbamic acid f-butyl ester... 

The reaction of the N-(5,5-dimethyl-3-oxo-l-cyclohexenyl)-N -arylcarbodiimides 41 with l-(L-pyrrolidino)cyclohexene affords a mixture of the [2+4] cycloadduct 42 (46 %) and the pyrrolidine adduct to the starting carbodiimide 43 (41 %). 

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