Sodium hydride → HCID 90134886, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve (2S)-1-azido-3-[(2-chloro-3-pyridyl)oxy]propan-2-ol (40.28 g, 176.17 mmol) in THF (880 mL) and slowly add sodium hydride (60% dispersion in mineral oil; 14.09 g, 352.35 mmol). Heat the mixture to 90° C. and stir for 2 hours at that temperature. Slowly pour the mixture into 1 liter of packed ice to quench the reaction. Remove the dioxanes under reduced pressure and extract the resulting mixture with EtOAc (3×). Dry the combined extracts over Na2SO4; filter; and concentrate the filtrate under reduced pressure. Purify via flash column chromatography using 2×330 g silica gel, eluting with a gradient of 0-75% of Et2O in hexanes. Combine the product fractions and remove solvents under reduced pressure to provide the title compound as a yellow solid (7.5 g., 22.15%). MS (m/z): 193 (M+1).

Provenance & Evidence