Journal of Organic Chemistry p. 3140 - 3143 (1986)
Update date:2022-09-26
Topics:
Thottathil, John K.
Moniot, Jerome L.
Mueller, Richard H.
Wong, Michael K. Y.
Kissick, Thomas P.
(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.
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