Sodium Iodide → 3-Boc-4(S)-cyclohexylmethyl-2,2-dimethyl-5(R,S)-iodomethyloxazolidine

Participants

Reaction Steps

2.4 g of Boc-2-cyclohexyl-1(S)-oxiran-2(R,S)-ylethylamine, 1.3 g of NaI and 1.1 ml of trimethylsilyl chloride are dissolved in 100 ml of acetonitrile, and the solution is stirred at R.T. for 1.5 h. Then 8.7 ml of a 1M solution of tetrabutylammonium fluoride in THF and 5.3 ml of dimethoxyethane are injected in. The mixture is stirred at R.T. for 2.5 h and then 200 ml of saturated aqueous NaHCO3 solution are added, and the mixture is extracted 3 times with 200 l of MTB. Drying over Na2SO4 and concentration in vacuo is followed by chromatography on silica gel (mobile phase MTB/diisopropyl ether 1:2) resulting in the title compound as a colorless oil.

Provenance & Evidence