2,6-Lutidine → HCID 58017529, compound

Participants

Reaction Steps

To a solution of ethyl (2R)-4-bromo-2-hydroxybutanoate (1.1 g, 5.2 mmol, prepared as described in J. Med. Chem. 2003, 46, 2057 or J. Am. Chem. Soc., 2004, 126, 12432 and Tetrahedron Letters 1997, 38, 4935-4938, in dry DCM (20 mL) at 0° C. was added Tf2O (1.62 g, 5.7 mmol) via syringe. After 5 min, 2,6-lutidine (0.67 g, 6.2 mmol) was added. After another 5 min, t-butylcarbazate (1.38 g, 10.4 mmol) in DCM (5 mL) was added. The solution was allowed to attain rt and stirred overnight. The solvent was evaporated and the residue was purified using flash chromatography (heptane/EtOAc 4:1, 3:1, 2:1) to give the slightly impure tert-butyl 2-[(1S)-3-bromo-1-(ethoxycarbonyl)propyl]hydrazinecarboxylate (1.65 g, 97%) as an oil.

Provenance & Evidence