292047-63-3

Upstream product

• 108-86-1 bromobenzene 
• 292047-60-0 (R)-3,4-dihydro-2,5-bis(methoxymethyl)-2H-pyrrole 1-oxide 
• 90290-05-4 (2R,5R)-2,5-bis(methoxymethyl)pyrrolidine 
• 292047-61-1 (2R,5R)-1-hydroxy-2,5-bis(methoxymethyl)-2-phenylpyrrolidine 

Downstream Products

• 292047-65-5 (2R,5R)-2,5-bis(methoxymethyl)-2,5-diphenylpyrrolidin-1-oxy radical 
• 292047-78-0 cis-2,5-bis(methoxymethyl)-2,5-diphenylpyrrolidin-1-oxy radical 
• 292047-76-8 (2S,5R)-2,5-Bis-methoxymethyl-2,5-diphenyl-pyrrolidin-1-ol 

Relevant academic research and scientific papers

Highly stereoselective synthesis of C2-chiral and meso nitroxides from an optically active pyrrolidine

Starting from (2R,5R)-2,5-bis(methoxymethyl)pyrrolidine 1, hydroxylamine cis-3 was synthesized with high stereoselectivity by successive oxidation and addition of PhMgBr. By using PhLi, trans (C2-chiral) pyrrolidine nitroxide trans-7 was obtained from nitrone 5 derived from hydroxylamine 3. The cis (meso) counterpart cis-7 was produced along with trans-7 when PhMgBr was employed in place of PhLi. Moreover, cis-7 was also obtained selectively by using PhLi and Et2AlCl with nitrone 5. The change of stereochemical bias observed when EtMgBr and/or nitrone 10 bearing an ethyl group were employed is also discussed. Copyright (C) 2000 Elsevier Science Ltd.