Process for the preparation of (r)-2-alkyl-3-phenyl-1-propanols

Details Process for the preparation of (r)-2-alkyl-3-phenyl-1-propanols Process for the preparation of (r)-2-alkyl-3-phenyl-1-propanols

C - Chemistry, Metallurgy

07

B

C07B 53/00 (2006.01) C07C 29/147 (2006.01) C07C 29/17 (2006.01) C07C 41/18 (2006.01) C07C 41/20 (2006.01) C07C 43/23 (2006.01) C07C 67/327 (2006.01) C07C 67/343 (2006.01) C07C 69/732 (2006.01) C07C 69/734 (2006.01)

Patent

CA 2414844

Compounds of formula (I), wherein R1 and R2 are, independently of one another, H,C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxy, C1-C6alkoxy-C1-C6alkyl, or C1- C6alkoxy-C1-C6alkyloxy, and R3 is C1-C6alkyl, are obtainable in high yiedls by stereoselective addition of R3-substituted propionic acid esters to R1- and R2- substituted benzaldehydes of formula R-CHO to form corresponding 3-R-3-hydroxy- 2-R3-propionic acid esters, conversion of the OH group to a leaving group, subsequent regioselective elimination to form 3-R-2-R3-propenic acid esters, and reduction to corresponding 3-R-2-R3-allyl alcohols and their enantioselective hydrogenation, wherein R is (a).

L'invention concerne des composés représentés par la formule (I), dans laquelle R¿1? et R¿2? représentent, indépendamment l'un de l'autre, H, C¿1?-C¿6? alkyle, C¿1?-C¿6? halogenalkyle, C¿1?-C¿6? alcoxy, C¿1?-C¿6-alcoxy-C¿1?-C¿6?alkyle, ou C¿1?-C¿6? alcoxy C¿1?-C¿6? alkyloxy, et R¿3? représente C¿1?-C¿6? alkyle. Ces composés peuvent être obtenus dans de grands rendements par addition stéréosélective d'esters de l'acide proprionique à substitution R¿3 à des benzaldéhydes à substitution R¿1? et à substitution R¿2? représentés par la formule R-CHO afin de former des esters d'acide 3-R-3-hydroxy-2-R¿3?-propionique, par conversion du groupe OH en un groupe partant, par élimination régiosélective subséquente afin de former des acides d'esters 3-R-2-R¿3?-propéniques, et par réduction en des alcools 3-R-2-R¿3?-allyliques et par hydrogénation énantiosélective de ces derniers, R représentant (II).

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