347386-37-2

Upstream product

• 69261-54-7 1-(benzyloxycarbonyl)pyrrolidin-2-ol 
• 121-45-9 phosphorous acid trimethyl ester 
• 14468-80-5 N-benzyloxycarbonylpyrrolidin-2-one 
• 88001-42-7 benzyl 2-methoxypyrrolidine-1-carboxylate 
• 1148-11-4 N-carbobenzyloxyproline 
• 501-53-1 benzyl chloroformate 
• 98782-97-9 1-benzyl 2-(4-nitrobenzyl) pyrrolidine-1,2-dicarboxylate 
• 78816-93-0 1-benzyl 2-(2,5-dioxopyrrolidin-1-yl) pyrrolidine-1,2-dicarboxylate 

Relevant academic research and scientific papers

Enzymatic and chromatographic resolution procedures applied to the synthesis of the phosphoproline enantiomers

The preparation of enantiomerically pure pyrrolidine-2-phosphonic acid (phosphoproline, ProP) has been addressed through the synthesis of suitable racemates and subsequent resolution by independent enzyme-catalyzed and chiral HPLC methods. First, racemic phosphoproline derivatives bearing the necessary protecting groups have been synthesized in excellent global yields starting from inexpensive materials. Preparative HPLC resolution of the N-Cbz-protected aminophosphonate on a cellulose-based column allowed the isolation of enantiomerically pure enantiomers on a gram scale. Enzyme-catalyzed alkoxycarbonylation of the aminophosphonate was studied using different lipases, solvents, and carbonates. Candida antarctica lipase type A (CAL-A) provided the highest enantioselectivity when combined with benzyl 3-methoxyphenyl carbonate.

Chemical conversion of cyclic α-amino acids to cyclic α-aminophosphonic acids

The oxidative decarboxylation of cyclic α-amino acids having urethane-type N-protecting groups with lead tetraacetate [Pb(OAc)4] gave 2-hydroxy derivatives, which were transformed into the corresponding α-aminophosphonic acid esters by treatment of trialkyl phosphites in the presence of Lewis acids. Deprotection and ester cleavage of the products in the usual manner afforded cyclic α-aminophosphonic acids. The convenient chemical conversion of five- and six-membered cyclic α-amino acids to the corresponding cyclic α-aminophosphonic acids has been accomplished.