Triphenylphosphine → (2S,3S)-3-pentyloxiran-2-ylmethyl 2-fluoro-6-(4-octyloxyphenyl)pyridin-3-yl ether

Participants

Reaction Steps

0.44 g (2.55 mmol) of diethyl azodicarboxylate is added dropwise at 0° C. to 0.67 g (2.55 mmol) of triphenylphosphine in 15 ml of tetrahydrofuran, and the mixture is stirred at room temperature for 30 minutes. 0.54 g (1.70 mmol) of 2-fluoro-3-hydroxy-6-(4-octyloxyphenyl)pyridine (prepared by EXAMPLE 3) and 0.25 g (1.70 mmol) of (2S,3S)-3-pentyl-2-oxiranylmethanol are then added. After a reaction time of 18 hours at room temperature, the solvent is distilled off, and the residue is purified by chromatography (silica gel, 8:2hexane/ethyl acetate ). Recrystallization from 8:2hexane/ethyl acetate gives 0.28 g of (2S,3S)-3-pentyloxiran-2-ylmethyl 2-fluoro-6-(4-octyloxyphenyl)pyridin-3-yl ether having an [α]D° (2.4% in CH2Cl2) of -15.75°. ##STR70##

Provenance & Evidence