Triethylamine → HCID 58743377, compound

Participants

Reaction Steps

To a cold (0° C.) solution of alcohol 94 (48 mg, 0.12 mmol) in CH2Cl2 (1.25 mL), Et3N (52 μL, 0.37 mmol) and MsCl (24 μL, 0.31 mmol) were added. After stirring for 2 h, the mixture was quenched with H2O (10 mL), extracted with CH2Cl2 (3×10 mL), dried over Na2SO4 and concentrated in vacuo. The crude mesylate was dissolved in DMF (0.65 mL) and NaN3 (40.5 mg, 0.62 mmol) was added. The mixture was stirred at 120 C. for 3 h and then quenched with H2O (10 mL), extracted with Et2O (3×10 mL), dried over Na2SO4 and concentrated in vacuo. The crude was purified by column chromatography on silica (hexane/EtOAc 10:1 to 5:1) to obtain azide 95 as a colorless oil (25 mg, 49% yield).

Provenance & Evidence