372159-52-9

Upstream product

• 372159-50-7 tert-butyl (4R)-4-[2-methoxy-6-(methoxymethoxy)benzyl]-2,2-dimethyl-1,3-oxazolidine 
• 57234-28-3 1-methoxy-3-(methoxymethoxy)benzene 
• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1255037-31-0 2-(2-amino-3-hydroxypropyl)-3-methoxyphenol 
• 372159-49-4 tert-butyl (4S)-4-{[(1H-imidazol-1-ylthiocarbonyl)oxy](2-methoxy-6-methoxymethoxy)phenylmethyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 372159-47-2 tert-butyl (4S)-4-[hydroxy(2-methoxy-6-(methoxymethoxy)phenyl)methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 

Relevant academic research and scientific papers

Biocatalytic enantioselective approach to 3-aryl-2-nitropropanols: Synthesis of enantioenriched (R)-5-methoxy-3-aminochroman, a key precursor to the antidepressant drug Robalzotan

The results of our studies on the biocatalytic enantioselective synthesis of different 3-aryl-2-nitropropanols are presented. These compounds could be obtained in moderate to good ee both bybaker's yeast mediated reduction of (E)-2-nitro-3-arylprop-2-en-1-ol precursors and by lipase kinetic resolution of racemic 3-aryl-2-nitropropanols. The synthesis of enantioenriched (R)-5-methoxy-3-aminochroman is also achieved. This important moietyispresent in different molecules active toward the central nervous system and is also the precursor for the synthesis of Robalzotan (NAD299), a potent 5-HT1A antagonist.

Synthesis of enantiomerically pure 3-aminochroman derivatives

Enantiomerically pure (3R)-amino-5-methoxy-3,4-dihydro-2H-1-benzopyran was successfully synthesised in nine steps starting from L-serine. The same synthetic pathway was used to prepare the (3S)-aminochroman derivative starting from D-serine. The enantiomeric purity of the final aminochroman derivatives was determined by capillary electrophoresis using β-cyclodextrin as the chiral selector.