2- Aminomethyl pyrrolidine

Chiral N,N-disubstituted 2-(aminomethyl)pyrrolidines as catalysts for asymmetric acylation of alcohols 99YGK598. 

C24H25NO 127927-43-9) see Saquinavir tris(trimethylsilyloxy)ethylene (CiiH2g03Si3 69097-20-7) see Saquinavir (-)-(S)-l-trityl-2-(aminomethyl)pyrrolidine (C24H26N2 98598-84-6) see Remoxipride 5 -0-trityl-2,3 -anhydro thymidine (C29H24N2O4 25442-42-6) see Zidovudine trityl chloride... 

Domination of the S-diastereomers for the dioxovanadium(V) Schiff base complexes being derivatives of aromatic orf/zo-hydroxyaldehydes or ketones and (S)-(+)-2-(aminomethyl)-pyrrolidine [35] was shown and the molar ratio of the diastereomers was determined by means of integration of the H signals.85... 

Methoxy-4,5-azimidobenzoic acid l-Allyl-2-aminomethyl pyrrolidine Phosphoric anhydride... 

Dimethoxy-5-sulfamoylbenzoic acid Carbonyldiimidazole l-Allyl-2-aminomethyl pyrrolidine... 

In Figure 14(b), the combination of proline and 2-aminomethyl pyrrolidine, the asymmetric transformation was observed but no preferential crystallization occurred. In Figure 14(c) only racemization was observed. Moreover, in Figure 14(d), non-coplanarity of the iminazoline and a-branched carbon prevented the double-bond shift and epimerization did not occur. 

Aminomethyl)pyrrolidines, 423 Aminophenols, 29-30 N-Aminopyrrolidine, 197 Ammonium cerium(IV) sulfate, 80-81 Ammonium persulfate-Silver nitrate,... 

Asymmetric hydrogenation. L-Proline has been convened into a series of (S)-2-(aminomethyl)pyrrolidines, such as (S)-2-(anilinomethyl)pyrrolidine (1), d + 19.7°, obtained as shown in equation (I). The product is an efficient chiral ligand for asymmetric reduction of various ketones by lithium aluminum hydride. 

Scheme 4 Synthesis of 4-(aminomethyl)pyrrolidin-3-one-0-methyloxime dihydrochloride...

High enantioselectivity has been achieved on addition of diethylzinc to benzaldehyde catalysed by a chiral diamine, (,S )-2-(A,A -disubstitutcd aminomethyl)pyrrolidine,116 and by chiral helical titanate complexes of tetradentate ligands.117 Enantioselective additions of dialkylzinc reagents to A,-(diphcnylphosphiiioyl)imines, promoted by aziridino alcohols,118 and to the carbon-nitrogen double bond of the nitrone 3,4-dihydroisoquinoline A-oxide, promoted by dicyclopentyl(R,R)-tartrate,119 have also been reported. 

Hong CY, et al. Novel fluoroquinolone antibacterial agents containing oxime-substituted (aminomethyl)pyrrolidines synthesis and antibacterial activity of 7-(4-(aminomethyl)-3-(methoxyimino)-pyrrolidin-l-yl)-l-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro[l,8]naphthyridine-3-car-boxylic acid (LB 20 304). J. Med. Chem., 1997, 40, 3584-3593. 

This clearly resembles the inhibition mode of the serine and cysteine protease inhibitors described above. Iterative refinement (Figure 1.18), e.g., by variation of ring size and symmetrization of the functional decoration pattern, combined with subsequent extrapolation of the renin-specific finding to the entire aspartate protease family, is the apparent basis for a new generation of nonpeptide, lead-like inhibitors with multiple therapeutically relevant endpoint opportunities. The five-membered 3,4-di(aminomethyl)-pyrrolidine (Figure 1.18) served as the core structure for highly active aspartate protease inhibitors [101]. 

Asymmetric rearrangement of cyclohexene oxide Cyclohexene oxide is rearranged to (S)-2-cyclohexene-l-ol in 92% ee by the chiral lithium amide (2) prepared from n-butyllithium and 1. Several related (S)-2-(disubstituted aminomethyl)pyrrolidines prepared from (S)-proline are almost as stereoselective.3... 

Proline derived (S )-2-(arylaminomethyl)pyrrolidincs. e.g., (.5)-2-(phcnylaminomethyl)pyrrolidine and (S)-2-l(2,6-dimethylphenyl)aminomethyl]pyrrolidine, are very effective modifiers for lithium aluminum hydride (Table 3, reagent F)68,69. 

In the presence of a nickel(II) catalyst, suUamates can be used as nitrogen sources for the intramolecular vicinal diamination of alkenes 141 (Scheme 16.37). While the mechanism of this oxidative transformation is not fully understood, the reaction bears the advantage that cyclic sulfamates 142 undergo selective deprotection under conventional conditions. Hence, this diamination protocol represents an attractive approach to free aminomethyl pyrrolidines (100). 

A special method for the synthesis of pyrrolo[l,2-a]quinoxalines using the PA4 synthon has not been developed. However, during the production of pyrrolo-1,4-benzodiazepines by the insertion of carbon monoxide into 2-[N-R-N-(2-bromophenyl)aminomethyl]pyrrolidines 187 in the presence of catalytic amounts of Pd(OAc)2 and PPhs pyrrolo[l,2-a]quinoxalines 190 were found together with other products formed as a result of the migration of, for example, an acyl group from the aniline nitrogen atom to the pyrrolidine nitrogen atom (Scheme 3.56) (Mory et al. 1984). 

Pyrrolidines have been prepared by 1,3-dipolar cycloaddition of N-(benzyli-dene)trimethylsilylamine/TMSOf 20 and methyl acrylate, N-methylmaleimide, or dimethyl maleate [35]. More recently, methyl trans-3-cyanociruiamate 1479 was reacted with N-benzyl-N-(trimethylsilylmethyl)aminomethyl methyl ether 1480 and trifluoroacetic acid in CH2CI2 at 0°C and 24°C to afford, via 1481, the pyrrolidine derivative 1482 in high yield and MeOSiMe3 13a [35a] (Scheme 9.20). Several... 

The final coupling reaction of l-cyclopropyl-6-fluoro-7-chloro-l,4-dihy-dro-4-oxo-l,8-naphthyridine-3-carboxylic acid (7a) and 4-( er -butoxycarbo-nylaminomethyl)pyrrolidin-3-one-0-methyloxime (15a) proceeds according to the methods described by Sanchez et al. [13], Domogala et al. [16], and Kimura et al. [17], followed by acid hydrolysis to afford gemifloxacin, 7 - (4 - (aminomethyl) - 3 - (methoxyimino)pyrrolidin -1 - yl) -1 - cyclopropyl - 6 -fluoro-4-oxo-l,4-dihydro[l,8]naphthyridine-3-carboxylic acid and other corresponding derivatives, according to Scheme 5. 

The carboxylic group of 6-aryl-2-methylthiopyrido[2,3- s1pyrimidine-7-carboxylic acid 563 was amidated with (i )-2-(aminomethyl)-l-( /t-butoxycarbonyl)pyrrolidine 564, followed by sulfide oxidation of the resulting amide 565 and reaction with 4-morpholinoaniline to give the substituted pyridopyrimidine 566 as a kinase inhibitor (Scheme 26) <2005W02005090344>. 

Preparation of (3R,4S)-3-aminomethyl-4,5-dimethyl-hexanoic acid 1-butyl ester and [4/ -[4/ (S )]]-4-(l,2-dimethyl-propyl)-pyrrolidin-2-one... 

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