Sodium Azide → HCID 86609126, compound

Participants

Reaction Steps

A solution of (R)-(8-(2,6-dichlorophenyl)-6-fluoro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate prepared in Example 57, step 7 (500 mg, 1.0 mmol) and sodium azide (340 mg, 5.2 mmol) in anhydrous DMF (20 mL) was heated at 90° C. under nitrogen for 20 hours. The cooled reaction mixture was quenched by the addition of water (20 mL) and the resulting suspension stirred vigorously for 5 minutes. The mixture was then partitioned between ethyl acetate (100 mL) and water (100 mL), the organic phase separated, washed with water (100 mL) and saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Column chromatography on silica gel with 10–25% ethyl acetate in hexanes afforded 310 mg (85%) of (R)-2-azidomethyl-8-(2,6-dichloro-phenyl)-6-fluoro-2H-chromene as a yellow oil. [α]D25=+282.1° (c=2.7 mg/0.7 MeOH); MS (EI) m/z 349. (M+).

Provenance & Evidence