Pyrrolidinone 5-methoxy

A variety of other substituents on the chain ends of polyethylene glycol) grafted onto polystyrene have been investigated for catalysis of the reaction of 1 -bromobutane and solid potassium phenoxide. The apparent activities of 2 % CL, 14% RS catalysts 56 (n = 4) wereZ = 2-(l,4-benzodioxanylmethyl) < tetrahydrofuran-2-yl < 2-pyri-dylmethyl < p-toluenesulfonyl < 8-quinolyl < 2-pyrrolidinon-l-yl < 2-methoxy-phenyl < 2-naphthyl179). 

SYNS E5110 3-((3,5-BIS(l,l-DIMETHYLETHYL)-4-HYDROXYPHENYL)METHYLENE)-l-METHOXY-2-PYRROLIDINONE 2-PYRROLIDINONE, 3-((3,5-BIS(l,l-DIMETHYLETHYL)-4-HYDROXYPHENYL)METHYL-ENE)-l-METHOXY-... 

Methoxy-4-methyl-l-phenyl-2-pyrrolidinone Typical Procedure22 ... 

Dihydroxypyrrolidinones, which can be considered as cyclic GABA derivatives, are potential nootropic drug candidates. All four possible diastereomers 794—797, as shown in Scheme 174, can be prepared from tartaric acid. Treating L-tartaric acid sequentially with acetyl chloride, methyl glycinate, and then acetyl chloride provides in 81% overall yield the C2-symmetric succinimide 790. In order not to reduce the methyl ester, the very mild treatment with sodium borohydride at —40 °C is employed to prepare the cw-hydroxylactam 791 in an 80% isolated yield. Esterification of 791 with trifiuoroacetic anhydride followed by triethylsilane reduction yields to the extent of 79% the pyrrolidinone 792. This is deprotected with sodium methoxide to provide in 97% yield (3i ,45)-3,4-dihydroxy-A -methoxy-carbonylmethyl-2-pyrrolidinone (793). Ammonolysis of 793 affords (3i ,4 S)-3,4-dihydroxy-2-oxopyrrolidine-A -acetamide (794) in 60% yield. Subsequent modifications to 793 allow for the preparation of (35, 4S)-3,4-dihydroxy-2-oxopyrrolidine-A/-acetamide (795), (3R,4R)-3,4-dihydroxy-2-oxopyrrolidine-A -acetamide (796) and (35, 47 )-3,4-dihydroxy-2-oxopyrrolidine-7V-acetamide (797) [234]. 

The first y-lactam analogs of penems were reported in 1986 [88, 89]. They were prepared from 5-methoxy-2-pyrrolidinone 146 using the Woodward s strategy for related penems [90] to build the fused ring system (Scheme 47). The y-lactam 150, which bears no side-chain, displays neither antimicrobial nor anti- 3-lactamase activity. 

In a similar related sequence, 2-pyrrolidinone was converted to the lactim ether (2-methoxypyrroline, 2.78) by treatment with dimethyl sulfate. This methoxy-imine was brominated with N-bromosuccinimide to give 2.79. Reaction with potassium acetate gave 2.80 and acid hydrolysis led to 2-hydroxy-4-aminobutanoic acid (2.2P).43... 

Hydroxy groups on either the oxazolidinone or pyrrolidinone rings could be functionalized easily (4, 5). We concentrated on conversion of the hydroxy to the acetoxy and the methoxy analogs. These conversions were straightforward and proceeded in high yield... 

C1 4H2 4MO3N4O13, Tetramethylammonium (/Li3 methoxy )-tris(/x methoxy )-tris(dicarbonyl-nitroso-molybdenum), 46B, 1165 Cl4H26O12S2Zn, Zinc hexa-aquo p-toluenesulphonate, 21, 585 C1 aH27Fi,N203Ta, Tetraethylammonium tetrafluoro(2-methylpyridine N-oxide)peroxotantalate(V), 43B, 1364 Cl5H28CI6CU4N3O5 C5H9NO, Mfl Oxa-hexa-/x"chloro-(aquo-copper(II))-tris(N-methyl-2-pyrrolidinone-copper(II)) N-methyl-2-pyrrolidinone solvate, 45B, 1216... 

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