L-Methylpyrrolidin-2-one

Addition products 444 are obtained from 3-(l -hydroxy-2,2,2,-trifluoroethyl-idenyl)-l-methylpyrrolidin-2-one and acylallene. They may further react with the C=0 group connected to CF3 to afford bicyclic compound 445 via intramolecular nucleophilic attack of oxygen on the C=0 group connected to CF3 and 446 via protonation of sodium enolate 444 [200],... 

Dimethyl and diethyl (l-methylpyrrolidin-2-ylidene)malonates (e.g., Scheme 38,467, n = 0, R = R1 = Me, Et R2 = H R4 = Me) and diethyl (l-methyl-l,2-dihydroquinolin-2-ylidene)malonate were obtained in 30-52% yields when l-methylpyrrolidin-2-one and 1-methyl-1,2-dihydroquinolin-2-one were first reacted with phosgene and then with dialkyl malonates in the presence of triethylamine in benzene at 60°C (61CB2278 69JA6683). 

Little is known on the metabolic fate of l-methylpyrrolidin-2-one (5.60), an industrial solvent also useful as a solubilizing agent and a penetration enhancer in topical formulations. A preliminary investigation of the disposition and metabolism of labeled l-methylpyrrolidin-2-one in the rat showed that the compound is excreted mainly in urine [171]. Three urinary metabolites were detected, the major of which (ca. 15% of the dose) was 4-(methylami-no)but-2-enoic acid (5.61). This unsaturated product may likely have been formed by H20 elimination from a hydroxylated metabolite. 

Bromo-5-methyl-l,6-naphthyridin-2-amine (53) with potassium O-ethylxanthate gave 8-methylthiazolo [4,5-b] L,6]naphthyridin-2(3//)-thione (54) (reactants, l-methylpyrrolidin-2-one, 165°C, 7h >95%) the 3-phenyl analog was made similarly.928... 

Trifluoroacetic anhydride is usually used without base " and derivatization of alcohols and polyols can be carried out without additional solvent. Pyridine bases should only be considered when phenols are trifluoroacetylated. Activation is possible w ith benzotri-azole/ l-methylpyrrolidin-2-one. pyridin-2-one, and pyridin-4-one, although the latter pyridinones are less effective than imidazole.Trifluoroacetyl acetate is less reactive than trifluoroacetic anhydride. Alternative reagents are trifluoroacetyl triflate " and the related trifluoroacetyl phosphate." ... 

The lithiated 7t-exTTF 924 was iodinated using perfluorohexyl iodide (PFHI) to give the iodo derivative 930. The latter took part in an Ullmann coupling using CuTC in l-methylpyrrolidin-2-one to afford the dimer 931 (Scheme 141) <2006CEJ2709>. 

The preparation of disaccharides, from benzyl-protected DISAL donors (e. g. 367,0 Scheme 61), was best carried out in l-methylpyrrolidin-2-one (NMP), a high polar, aprotic solvent. 

Cyclobutanone tosylhydrazone has been reported to react with sodium methoxide in diethylene glycol or l-methylpyrrolidin-2-one to give methylenecyclopropane 40 (79-80%) from ring contraction, cyclobutene (18-20%) from hydrogen migration and buta-1,3-diene (1-2%) from ring opening. 

Ketones. Grignard reagents can be converted into ketones by reaction with Fe(CO)s in THF (25°, 1 hour) and then with an alkyl iodide (25°). Yields are somewhat improved by addition of l-methylpyrrolidine-2-one to the solution. ... 

Methyl-2-pyrrolidone see l-Methylpyrrolidin-2-one N-Methylpyrrolidone see l-Methylpyrrolidin-2-one alpha.-Methylstyrene see Isopropenylbenzene Methyl sulfoxide see Dimethyl sulfoxide... 

Nitrous oxide see Dinitrogen oxide NM see Nitromethane NMF see N-Methylmethanamide NMP see l-Methylpyrrolidin-2-one l,l)l)2,2,3,3,4,4-Nonafluorohexane... 

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