1- Aminopyrrolidines

Both the infrared and ultraviolet spectra of pyrrolidine-2,3,5-triones (75) have been interpreted to support their existence as hydroxy-maleimides (76), and the occurrence of a strong OH stretching band in the infrared spectrum of 4-phenylpyrrolidine-2,3,5-trione has been taken as evidence that it too exists in a hydroxy form, probably 76 (R CeHg). However, the trioxo formulation is suggested by t/j the infrared spectra of jV-substituted pyrrolidine-2,3,5-triones, although an equilibrium apparently occurs depending upon the substituents and conditions. The zwitterion formulation 77 has been advanced for 4-aminopyrrolidine-2,3,5-trione. For chemical evidence... 

AO AP AP/AO ASB ASME ASTM 1-AP ATMP AVAT AVP All-Organic 5-aminopentanol All-Polymer/All-Organic Shell Boiler Makers Association (UK) American Society of Mechanical Engineers American Society for Testing and Materials 1 -aminopyrrolidine aminotri-(methylenephosphonic acid) All-Volatile alkaline treatment All-Volatile programs... 

Finally, a lead optimization program that utilized a strategy to maximize LipE in a series of aminopyrrolidines produced the broadly selective, potent adenosine-5 -triphosphate (ATP)-competitive Akt inhibitor 11 (Akt IC50 < 1 nM, clogP = 2.4, LipE = 7.2) which was nominated for clinical development [18]. 

JOC8210>. Condensation of succinaldehyde with arylhydrazines and benzotriazole gives 1-aminopyrrolidines 646 that upon treatment with organomagnesium reagents rearrange to 1,4,5,6-tetrahydropyridazines 647 <1998S1627>. 

Quinolones possessing a 7-(3-aminopyrrolidin-l-yl) substituent are particularly potent antibacterial agents. However, they often have very low solubility. Based on the observations that the hydroxymethylpyrrolidine (38) is significantly more potent against bacteria than its enantiomer (39) (the hydroxymethyl substituent in (39) apparently has a deleterious effect on activity while the same substituent in (38) has little effect on potency based on comparisons with the unsubstituted pyrrolidine analogue (40)) [84] and the enantiomer (41) is at least as potent as,... 

Among other enantioselective alkylations, a series of 3-aminopyrrolidine lithium amides (67 derived from 4-hydroxy-L-proline) have been used to induce high ee% in the addition of alkyllithiums to various aldehydes. Structure-activity relationships are identified, and the role of a second chiral centre (in the R group) in determining the stereochemistry of the product is discussed. 

Enantiomeric excesses of up to 76% have been obtained for alkyllithium-aldehyde condensations using 3-aminopyrrolidine lithium amides as chiral auxiliaries. Addition of organolithiums to imines has been achieved with up to 89% ee, in the presence of C2-symmetric bis(aziridine) ligands. ... 

A fragmentation reaction which appears to proceed via the generation of 1,4-diradicals is the decomposition of 1,1-tetramethylenediazenes. Unlike the more stable 1,2-diazenes (tetrahy-dropyridazines, see Section 4.2.1.), the 1,1-isomers are not usually isolated or characterized by physical methods but are proposed as intermediates in the thermal decomposition of iV-phenyl-sulfonamidopyrrolidines 1, giving 1,4-diradicals which recombine to yield cyclobutanes 3 and 4. 39 These intermediates are also formed in the photochemical decomposition at low temperature of 1,1-tetramethylenediazenes, prepared in situ from 1-aminopyrrolidines and /er/-butyl hypochlorite.141... 

Resolution of 3-aminopyrrolidine is reported in the hterature using diben-zoyltartaric acid via a 2 1 salt. We found that the (R)-enantiomer of the IN-Boc protected racemate could be crystallized in 32% yield and 99.5% ee from ethanol in a single crystallization with 0.25 mol equivalents of (R,R)-dibenzoyltartaric acid (Scheme 13.9). Other solvents tested gave poorer results. 

Polyaniline-supported Co(II) catalyst 41 was used to catalyze the epoxidation of various alkenes under oxygen atmosphere at ambient temperature.61 63 One report61 described a synthesis of a-hydroxy- 3-aminopyrrolidine amides as potential HIV protease inhibitors (Scheme 1). In this synthesis, catalyst 41 also mediated epoxide ring opening of the epoxide intermediate by an aniline to afford the desired product. 

The intramolecular amino- and amido-mercuration of <5-unsaturated-/J-amino-amines and carbamates 293 have been found to afford the corresponding 3-aminopyrrolidines... 

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