Sharpless asymmetric catalytic dihydroxylation of 4-allylanisole (I) using (DHQD)2AQN as the chiral ligand provided diol (II). Condensation of diol (II) with trimethyl orthoacetate in the presence of pyridinium tosylate, followed by treatment with acetyl bromide, afforded bromo ester (III), which was subsequently transformed into the chiral epoxide (IV) with K2CO3 in MeOH. Epoxide (IV) opening with 4-(4-methylbenzyl)piperidin-4-ol (V) gave amino alcohol (VI). The methyl ether group of (VI) was finally cleaved by treatment with boron tribromide.