93715-74-3Relevant academic research and scientific papers
Lewis Acid-Catalyzed Addition of Benzophenone Imine to Epoxides Enables the Selective Synthesis and Derivatization of Primary 1,2-Amino Alcohols
Leitch, David C.,Lim, John Jin
, p. 641 - 649 (2018/05/14)
Benzophenone imine was found to be an effective ammonia surrogate for the selective preparation of primary 1,2-amino alcohols from epoxides, including enantiopure epichlorohydrin, in the presence of catalytic Y(OTf)3. High-throughput screening of 48 Lewis acids quickly identified Y(OTf)3 as an effective mediator of the addition reaction under mild conditions. Following acidic hydrolysis, the primary amino alcohol salt is revealed and partitions into the aqueous solution, while the benzophenone byproduct is easily removed by simple extraction with ethyl acetate. These ammonium salts can be directly Boc-protected or further derivatized without isolation to form benzamides and sulfonamides under Schotten-Baumann-type conditions in up to 79% isolated yield over three steps. This methodology has been used to prepare key intermediates for the synthesis of PRMT5 inhibitors with high enantiopurity as well as numerous other amide and sulfonamide derivatives.
dl-Isoserine and Related Compounds
Williams, Theresa M.,Crumbie, Robyn,Mosher, Harry S.
, p. 91 - 97 (2007/10/02)
Syntheses of dl-isoserine (3-amino-2-hydroxypropanoic acid, 7) and further functionalized derivatives are described.Reaction of glyoxylic acid with nitromethane gives the known 2-hydroxy-3-nitropropanoic acid (8), which upon hydrogenolysis affords dl-isoserine in high yield.The comparable nitro-aldol reaction of 3-nitropropanal ethylene acetal (2) with glyoxylic acid produces 2-hydroxy-3-nitro-5-oxopentanoic acid ethylene acetal (4a) as a mixture of erythro and threo isomers.The methyl esters of hydroxy acid 4a are chromatographically separable as the tert-butyldimethysilyl ethers.Catalytic reduction (Pd/C) of these nitro compounds gives the corresponding methyl 3-amino-2-hydroxy-5-oxopentanoate ethylene acetals 9.Ethyl 2-hydroxy-3-phthalimidopropanoate (22) and ethyl 2-oxo-3-phthalimidopropanoate (23) were also prepared along with several other N-protected β-amino-α-oxy esters related to isoserine.
