2,6-Lutidine → phenylmethyl 2-{(1S)-3-iodo-1-[(methyloxy)carbonyl]propyl}hydrazinecarboxylate

Participants

Reaction Steps

To a solution of methyl (2R)-2-hydroxy-4-iodobutanoate (3.35 g, 13.7 mmol) in DCM (100 mL) under N2 at −70° C. was added 2,6-lutidine (5.67 g, 55 mmol), followed by triflate anhydride (4.07 g, 144.4 mmol) dropwise. Stirring continued at the same temperature for 1 hour. Phenylmethyl hydrazinecarboxylate (2.74 g, 16.5 mmol) was added in one portion, and the reaction mixture was allowed to warm up to room temperature and stirred for 24 hours. The reaction mixture was concentrated, and the crude oil was purified by column chromatography (PE:EA=20:1 to 1:1) to provide phenylmethyl 2-{(1S)-3-iodo-1-[(methyloxy)carbonyl]propyl}hydrazinecarboxylate as yellow oil (3.7 g, 83%). 1H NMR (300 MHz, CDCl3) δ 7.35-7.34 (m, 5H), 6.51 (s, 1H), 5.13 (s, 2H), 4.27 (s, 1H), 3.76-3.70 (m, 4H), 3.42-3.30 (m, 2H), 2.25-2.06 (m, 2H).

Provenance & Evidence