Toluene → HCID 68770390, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2R,3R)-3-(tert-butyl-dimethyl-silyloxy)-3-(4-chloro-phenyl)-2-methyl-propionic acid (0.93 g, 2.8 mmol) in THF (30 mL) at 0° C. was added Et3N (0.438 mL, 3.1 mmol) followed by ethyl chloroformate (0.30 mL, 3.1 mmol). The solution was stirred for 1 h at 0° C., and a solution of NaN3 (552 mg, 8.5 mmol) in water (10 mL) was added. The reaction solution was stirred for 4 h with warming to rt. The mixture was poured into water and extracted with Et2O (3×). The combined organic extracts were dried (MgSO4) and concentrated to afford the crude acyl azide. A mixture of the acyl azide, tert-butanol (10 mL), and toluene (20 mL) was heated at reflux for 12 h. The reaction mixture was cooled and concentrated, and the residue was purified by flash chromatography (EtOAc/hexanes) to provide the desired product as a colorless oil (354 mg, 31%). 1H NMR (400 MHz, CDCl3): 7.28 (s, 4H), 4.90 (br s, 1H), 4.60 (br d, J=8.0, 1H), 3.77-3.65 (m, 1H), 1.46 (s, 9H), 0.94 (s, 9H), 0.88 (d, J=6.8, 3H), 0.06 (s, 3H), −0.13 (s, 3H).

Provenance & Evidence