103201-82-7Relevant articles and documents
Conversion of L-Pyroglutamic Acid to 4-Alkyl-Substituted L-Prolines. The Synthesis of trans-4-Cyclohexyl-L-proline
Thottathil, John K.,Moniot, Jerome L.,Mueller, Richard H.,Wong, Michael K. Y.,Kissick, Thomas P.
, p. 3140 - 3143 (2007/10/02)
(S)-5-(Hydroxymethyl)-2-pyrrolidinone (3), prepared from L-pyroglutamic acid, was condensed with benzaldehyde to obtain the O,N-acetal 4 in excellent yield.Alkylation of 4 with 3-bromocyclohexene followed by reduction gave trans-4-cyclohexyl-L-prolinol (7) in good chemical yield with excellent stereoselectivity.Sequential N-protection, oxidation of the alcohol to the acid, and N-deprotection furnished trans-4-cyclohexyl-L-proline (1) in excellent yield and quality.Compound 1 serves as an intermediate for the preparation of ACE inhibitors including Fosenopril.