Reference

Process for preparation of cis-(oxazolylmethoxy)(arylmethoxy)cycloalkanes via acylation/desymmetrization of cycloalkanediols

Process for preparation of cis-(oxazolylmethoxy)(arylmethoxy)cycloalkanes via acylation/desymmetrization of cycloalkanediols. Salagnad, Christophe; Zocher, Frank; Burgard, Andreas; Junker, Bernd; Hoerlein, Rolf-Ludwig; Stuedemann, Thomas; Maier, Claus-Juergen; Hachtel, Jochen; Holla, Wolfgang; Tappertzhofen, Christoph; Kulitzscher, Berndt; Mutti, Stephane (Sanofi-Aventis Deutschland G.m.b.H., Germany). Ger. Offen. DE 102004040736 A1 2 Mar 2006, 36 pp.Several reagents such as 832-09-7 is used here. (German). (Germany). CODEN: GWXXBX. APPLICATION: DE 2004-102004040736 23 Aug 2004. DOCUMENT TYPE: Patent CA Section: 28 (Heterocyclic Compounds (More Than One Hetero Atom)) Title compds. [I; A = C3-8 cycloalkyl, cycloalkenyl in which 31 C atom may be replaced by O; R1, R2, R4, R5 = H, F, Cl, Br, OH, NO2, CF3, OCF3, alkyl, alkoxy; R3 = H, (substituted) alkyl, PhCH2; X, Y = (O-interrupted) alkylene], were prepd. in a multistep process starting with either enzymic monodeprotection of diprotected cycloalkanediols or enzymic monoacylation of cycloalkanediols followed by protecting group interconversion, alkylation, and sapon. steps. Thus, cis-1,3-diacetoxycyclohexane (prepn. given) was stirred with Chirazyme L2 in phosphate buffer at pH 6.8 at 35-75° to give 87% (1S,3R)-1-acetoxycyclohexan-3-ol in >99% enantiomeric excess. This was THP-protected, deacetylated, alkylated with 4-chloromethyl-2-(4-fluorophenyl)oxazole, deprotected, alkylated with Me 2-bromomethyl-6-methylbenzoate, and sapond. with KOH in Me3COH to give title compd. (II). .