Triacetoxyperiodinane → HCID 57945204, compound

Participants

Reaction Steps

To a solution of (1R,2S)-ethyl 1-(tert-butoxycarbonylamino)-2-(2-hydroxyethyl)cyclopropanecarboxylate (9.70 g, 35.5 mmol) in DCM (300 ml) at 0° C. was added Dess-Martin periodinane (18.06 g, 42.6 mmol). The formed slurry was stirred at room temperature overnight. The reaction mixture was filtered through celite. The resulting filtrated was concentrated and this process was repeated one more time. Residue was purified by a silica gel column, eluted with 8:1, 4:1, 3:1, then 2:1 heaxane-EtOAc to yield (1R,2S)-ethyl 1-(tert-butoxycarbonylamino)-2-(2-oxoethyl)cyclopropanecarboxylate (6.15 g, 22.67 mmol, 63.9% yield) as a colorless oil. 1H NMR (CDCl3) δ 1.24 (t, J=7 Hz, 3H), 1.40-1.45 (m, 11H), 1.65-1.69 (m, 1H), 2.75-2.80 (m, 2H), 4.09-4.19 (m, 2H), 5.17 (b, 1H), 9.76 (s, 1H).

Provenance & Evidence