Pyrrolidinone 3- -, crystal

Preparation of 4-( -Chloroethyl)-3,3-Diphenyl-1Ethyl-2-Pyrrolidinone A solution of a,a -diphenyl-a -(1-ethyl-3-pyrrolidyl)-acetonitrile in 70% sulfuric acid was heated at 130°-140°C for 48 hours, poured onto ice, made basic with sodium hydroxide, and extracted with chloroform. The chloroform solution was acidified with hydrogen chloride gas, dried over sodium sulfate and concentrated. The residue was refluxed in 500 ml of thionyl chloride for 3 hours the resulting solution was concentrated in vacuo and the residue was crystallized from isopropyl ether. 

C) Preparation of Doxapram Hydrochloride [3,3-Diphenyl-1-Ethyl-4-(2-Morpholino-Ethylj-2-Pyrrolidinone Hydrochloride Monohydrate] A solution of 25 grams (0.076 mol) of 4-(2-chloroethyl)-3,3-diphenyl-1-ethyl-2-pyrrolidinone and 13.3 grams (0.153 mol) of morpholine in 500 ml of absolute ethanol was heated at 95°-120°C for 21 hours in a closed system and concentrated in vacuo. The residue was dissolved in 3(X) ml of two normal hydrochloric acid and extracted with 150 ml of ethyl acetate. A solid crystallized (13 g) during the extraction and was removed by filtration. MP 217°-219°C. The acid extracts were made basic with sodium hydroxide and extracted with ether, and the ether solution was concentrated in vacuo and the residue was suspended in six normal hydrochloric acid. Additional crystalline product formed and was recrystallized from two normal hydrochloric acid. Yield, 10 grams MP 217°-219°C. Total yield, 23 grams (70%). 

The first solid-state linear dimerization was observed with N-vinylpyrrolidi-none. It was first quantitatively converted to its Markovnikov HBr addition product (by application of HBr gas at -40 °C), which upon warming to room temperature lost HBr and formed ( )-l,r-(3-methyl-l-propene-l,3-diyl)bis-(2-pyrrolidinone), but the yield was less than 100% [58]. Interestingly, such head-to-tail dimerizations of alkenes lead to shrinking and that may create reactivity even if the crystal lattice does not allow for molecular migrations due... 

C. Preparation of 2-oxo- l-phenyl- i-pyrrolidinecarboxylic acid (3). To 1.70 g (10 mmol) of spiroacylal 2 was added 2.79 g (3 mmol) of aniline. The mixture became a homogeneous orange solution after 15 min and was allowed to stir at room temperature for 12 hr. The resulting crystalline mass was diluted with 150 mL of chloroform, washed three times with 10 mL of aqueous 10% hydrochloric acid, washed once with 20 mL of brine, dried (MgS04), and decolorized with a small amount of activated carbon. Concentration of the organic layer by rotary evaporation gave 5.27 g of a brown residue, which was recrystallized from chloroform-hexane to afford 4.86-5.07 g (79-82%) of the pyrrolidinone 3 as white crystals, mp 146-148°C (dec) (Note 4). 

The pyrrolidinone and piperidinones (Tab. 5.2, n=l and n=2, respectively) had similarly impressive potencies, establishing that such cyclization led to increased potency, and also that inhibition was not extremely sensitive to ring size in this series. As described above, the binding modes observed for the pyrrolidinones (Tab. 5.2, n=l) in the cathepsin K complex crystal structures seem fairly consistent with previous structures observed with acydic compounds bound (Fig. 5.5). Unfortunately the 5- and 6-membered cyclic diaminoketones shared the undesir-... 

Two different approaches to ( —)-statine (831), an unusual amino acid component of pepstatine, both employ 793c as their starting point. In the first synthesis (Scheme 120) [183], reduction of 793c with sodium borohydride produces a mixture of two isomeric 5-hydroxy-pyrrolidinones, from which the pure cis product 824 crystallizes in 85% yield. Conversion of bisacetate 825 to thioether 826 followed by removal of the acetate and silylation of the resulting alcohol affords 827. Radical cyclization of 827 produces a 3 2 mixture of isomers 828. Desilylation and debenzylation gives 829 as a single diastereomer. The Boc-protected intermediate 830 intersects with a known synthesis of ( —)-statine (831). 

Besides the above materials, imsaturated ultra low molecular weight (ULMW) poly (L-lactide) (PEA) (ULMW PLA), can also be used as an injectable in situ crosslinkable macromer for tissue engineering. Jabbari and He mixed ULMW PLA with fumaryl chloride to make unsaturated in situ crosslinkable poly (lactide fumarate) (PLAF) macromer. When this PLAF macromer was injected and crosslinked widi l-vinyl-2-pyrrolidinone (NVP) in the presence of NaCl crystals as porogen, porous scaffold was formed in situ (Jabbari and He, 2008). These porous scaffolds showed osteoconductive behavior and led to new bone formation when implanted in nude mice. 

Perfluorinated Nafion ionomer/ PVDF blends Dimethylformamide, dimethylacetamide, l-Methyl-2-pyrrolidinone The spherulitic crystalline moiphology of PVDF showed strong dependence on the casting temperature and compositions. Mixed a- and y-forai crystals were obtained. DSC, SAXS, microscope, dielectric thermal analyzer (Kyu and Yang 1990)... 

White, T.J., Liechty, W.B., Natarajan, L.V., Tondiglia, V.P., Bunning, T.J., Guymon, C.A. The influence of N-vinyl-2-pyrrolidinone in polymerization of holographic polymer dispersed liquid crystals (HPDLCs). Polymer 47, 2289-2298 (2006)... 

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