Synthesis of trans-epoxy-L-Proline (cas 147-85-3) and cis-aziridino-L-Proline (cas 147-85-3) from S-pyroglutamic acid. Regio- and diastereoselective ring opening of its derivatives

Add time:09/30/2019    Source:infona.pl

The pyroglutamic acid derivative 4 was converted through several steps into 2S,3R,4S-epoxyproline 8. Key steps of the reaction sequence were the stereoselective epoxidation of 4 to 5 and the chemoselective reduction of the amide group of 5 with concomitant transformation of the acetal moiety into the N-benzyl protecting group without oxirane ring opening. The air sensitive benzyl derivative was transformed to the stable N-Boc prolinol derivative 6. Oxidation of 6 gave the protected epoxyproline derivative 7. Deprotection of 7 furnished enantiopure 2S,3R,4S-epoxyproline 8. Ring opening of the oxirane 6 or 16 was accomplished with C, N, Cl-nucleophiles under complete regiocontrol. Azidoprolinol 9 served as a starting material for the synthesis of epiminoproline derivative 23.

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