3-Hydroxypyridine → methyl (S)-8-(benzyloxy)-4-[2-(3-pyridyloxy)ethyl]octanoate

Participants

Reaction Steps

To a solution of methyl (S)-8-(benzyloxy)-4-(2-hydroxyethyl)octanoate (1.61 g, 5.2 mmol) in methylene chloride (20 ml) is added 3-hydroxypyridine (0.51 g, 5.4 mmol) and triphenylphosphine (1.82 g, 7 mmol). The mixture is stirred at room temperature for 10 minutes and then diisopropyl azodicarboxylate (1.05 ml, 5.3 mmol) is added slowly. The mixture is allowed to stir for 2 hours and the solvent is evaporated. The residue is purified by flash chromatography on silica gel using 1:1 ethyl acetate/hexane as eluent to obtain methyl (S)-8-(benzyloxy)-4-[2-(3-pyridyloxy)ethyl]octanoate; IR (CH2CL2): 1732, 1280, 1230, 1102 cm-1.

Provenance & Evidence