Methyl iodide → Tert-butyl n-[1-(r/s)-(iodomethyl)undecyl]carbamate

Participants

Reaction Steps

Trimethylphosphine (1.0M, 1.33 mmol) was added dropwise to a stirred solution of (azodicarbonyl)dipiperidine [ADDP] (336 mg, 1.33 mmol) in abs. THF (25 ml) at 0° C. After 30 minutes, iodomethane (189 mg, 1.33 mmol) and tert-butyl N-[1-(R/S)-(hydroxy-methyl)undecyl]carbamate 46 (200 mg, 0.664 mmol) were added to the solution, which was subsequently stirred for 4 hours at room temperature. The precipitate was then filtered off and the solution evaporated to dryness. The residue was dissolved in ethyl acetate and the remaining hydrazide was precipitated from hexane and removed by filtration. Following evaporation, the residue was taken up in CH2Cl2 (50 ml), washed with water (2×25 ml) and with NaHCO3 (sat, aq) (1×25 ml), dried with MgSO4, filtered and evaporated. The residue was purified by column chromatography in hexane:ethyl acetate 4:1 (v/v) to give 62 (176 mg, 64%).

Provenance & Evidence