91247-38-0Relevant academic research and scientific papers
A simple synthesis of β-alkyl-substituted β-amino acids
Lazar, Laszlo,Martinek, Tamas,Bernath, Gabor,Fueloep, Ferenc
, p. 219 - 224 (2007/10/03)
By the condensation of branched-chain aliphatic or alicyclic aldehydes with malonic acid in the presence of ammonium acetate, β-alkyl-substituted β-amino acids were prepared.
SYNTHESIS OF 6-ARYL-4-HYDROXYPIPERIDIN-2-ONES AND A POSSIBLE APPLICATION TO THE SYNTHESIS OF A NOVEL HMG-CoA REDUCTASE INHIBITOR
Ashton, Michael J.,Hills, Susan J.,Newton, Christopher G.,Taylor, John B.,Tondu, Sylvie C. D.
, p. 1015 - 1035 (2007/10/02)
A series of 6-aryl-4-hydroxypiperidin-2-ones (11a-11g) were synthesised with the key step being a Dieckmann cyclisation of the appropriate methyl 3-(ethoxycarbonylacetylamino)-3-(substituted) propionate (8a-8g) and this new synthetic route was successfully applied to the synthesis of 4-hydroxy-6-(2-phenylethyl)piperidin-2-one (11h).The application of this strategy to the synthesis of the putative HMG-CoA reductase inhibitor 6--4-hydroxypiperidin-2-one (11i) was attempted, but failed during the Dieckmann cyclisation of methyl 3-(ethoxycarbonylacetylamino)- 3-propionate (8i).An alternative synthesis of a 1:1 diastereomeric mixture of (11i) was achieved by the reductive cleavage of the isoxazoline (24) with Raney nickel.The mixture of diastereoisomers (11i) was inactive in-vitro and in-vivo (rat) against HMG-CoA reductase
