Isopropyl iodide → Latanoprost

Participants

Reaction Steps

A mixture of Latanoprost acid (0.95 g, 2.4 mmol), isopropyl iodide (0.83 g, 4.8 mmol), cesium carbonate (1.20 g, 3.6 mmol) and DMF (20 mL) was stirred for 2–3 hours at 40–50° C. (TLC monitoring) and poured into a stirred mixture of 2 M aqueous NaHSO4 (2.5 mL, 5 mmol), ice (50 mL) and ether (50 mL). The organic layer was separated and the water phase was extracted with ether (2×50 mL). The combined organic layers were washed with brine (50 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure to give 1.05 g (100% yield) of crude product. The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate 1:1 v/v) to give Latanoprost. 1H NMR (CDCl3) is compatible with literature data.

Provenance & Evidence