4-Benzyloxyphenol (I) was protected as the silyl ether (II) upon treatment with tert-butyldiphenylsilyl chloride and imidazole. Then, benzyl ether cleavage in (II) by means of transfer hydrogenolysis with cyclohexene and Pd/C furnished the silyloxy phenol (III). Coupling of phenol (III) with (R)-glycidol (IV) under Mitsunobu conditions yielded the intermediate glycidyl ether (V).
The aliphatic amino group of 4-aminophenethylamine (VI) was regioselectively protected as the N-Boc derivative (VII) using Boc2O. Subsequent reductive alkylation of aniline (VII) with N-benzyl-4-piperidone (VIII) afforded the anilinopiperidine (IX). The N-benzyl group of (IX) was then removed by transfer hydrogenolysis, and the resulting piperidine (X) was condensed with octyl isocyanate (XI), yielding the corresponding urea (XII). After acidic cleavage of the N-Boc protecting group of (XII), the primary amine (XIII) was condensed with the intermediate epoxide (V) to produce the amino alcohol (XIV). Final desilylation of (XIV) gave rise to the title compound.