26458-37-7

Upstream product

• 26458-36-6 methyl 2-methyl-5-oxo-1-phenyl-4-(phenylamino)-2,5-dihydro-1H-pyrrole-2-carboxylate 

Downstream Products

• 141214-25-7 methyl 3,3-(ethylenedioxy)-5-methyl-2-oxo-1-phenylpyrrolidine-5-carboxylate 
• 141214-37-1 3-hydroxy-5-hydroxymethyl-5-methyl-1-phenylpyrrolidin-2-one 
• 141214-35-9 3,3-(ethylenedioxy)-5-hydroxymethyl-5-methyl-1-phenylpyrrolidin-2-one 
• 141214-36-0 8-Hydroxymethyl-8-methyl-7-phenyl-1,4-dioxa-7-aza-spiro[4.4]nonane-6-thione 
• 141214-26-8 methyl 3,3-(ethylenedioxy)-5-methyl-1-phenyl-2-thiopyrrolidine-5-carboxylate 
• 141214-29-1 8-Methyl-7-phenyl-1,4-dioxa-7-aza-spiro[4.4]nonane-8-carboxylic acid methyl ester 

Relevant academic research and scientific papers

The influence of α-amido/thioamido functionality in ester reduction with sodium borohydride

Sodium borohydride in methanol smoothly reduces the esters of α-amino acids having N-acyl (orthioacyl)-N-alkyl (-NRCOR′ or -NRCSR′) substituents, producing amino alcohol derivatives. Esters with α-NHCOR or-CONRR′ functionality however remain unaffected. Electron-withdrawing property of the substituent appears to play a crucial role, anion formation with -NHCOR group perhaps diminishing its effect.

A convenient reduction of substituted amino-acid esters

Esters having N-alkyl-N-acyl (orthioacyl) functionality at the α-position are smoothly reduced with NaBH4-MeOH at 0-5°C in very good yields.