Methyl iodide → Boc-L-Pro-Ome

Participants

Reaction Steps

N-(tert-Butoxycarbonyl)-L-proline (7.05 g, 0.0328 mol) was dissolved in THF (200 mL, 2 mol) and to this solution was added potassium carbonate (10.2 g, 0.0738 mol) and methyl iodide (5.0 mL, 0.08 mol). The resulting heterogeneous solution was heated to reflux for 16 h with vigorous stirring. The mixture was then filtered through a pad of diatomaceous earth and the filter pad was washed thoroughly with tetrahydrofuran (THF). The volatiles were removed in vacuo and the resulting residue was purified by CombiFlash chromatography using a 40 g column and eluting with EtOAc/hexanes (0-25%) to afford the desired product as a yellow oil (7.3 g, 97%). LC-MS: 130.2 (M−Boc+2H)+ and 252.1 (M+Na)+.

Provenance & Evidence