Methyl iodide → HCID 60067022, compound

Participants

Reaction Conditions

Reaction Steps

To (2S,4R)-2-Hydroxymethyl-4-trimethylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester in 10 mL of acetone was added iodomethane 0.86 mL (13.5 mmol), silver oxide 3.04 g (13.2 mmol) and the solution was warmed to 57° C. for 8 h. The mixture was cooled to 25° C., filtered through celite and concentrated. The residue was taken up in 50 mL of EtOAc and was washed with Sat. NaHCO3 (2×50 mL). The organic layer dried over Na2SO4 and concentrated. The residue was loaded onto 50 mL silica and eluted with Hexane:EtOAc (3:7). The purified fraction were concentrated to give 0.66 g (67%) of (2S,4R)-2-Methoxymethyl-4-trimethylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester as clear oil. HPLC: Rt 3.43 min. (98.2% area). 1H NMR (CDCl3, 300 MHz) δ: 7.38-7.32 (5H, m), 4.70 (2H, s), 4.56-4.46 (2H, m), 4.18-4.13 (2H, m), 3.86 (1H, q, J=5.5 Hz), 3.07-3.02 (1H, m), 1.99-1.95 (1H, m), 1.61 (3H, bs), 1.57-1.52 (1H, m), 0.12 (9H, s). LCMS (ESI) (M+H+) m/z: 338.2.

Provenance & Evidence