Sodium hydride → HCID 66874260, compound

Participants

Reaction Steps

To a solution of tert-butyl 6,9-diazaspiro[4.5]decane-9-carboxylate (192 mg, 0.80 mmol) in DME (10 mL) was added NaH (60%, 96 mg, 2.4 mmol). The reaction mixture was stirred at room temperature for 10 min, followed by addition of methyl 2-chlorobenzoxazole-4-carboxylate (186 mg, 0.88 mmol). The reaction mixture was stirred at room temperature for 20 h. The reaction was quenched by adding 5 mL of H2O and extracted with EtOAc (2×30 mL). The organic layer was washed by brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, 50-100% chloroform in hexane) to afford methyl 2-(9-(tert-butoxycarbonyl)-6,9-diazaspiro[4.5]decan-6-yl)benzoxazole-4-carboxylate (61.4 mg, 18.5%) as yellow oil. MS consistent.

Provenance & Evidence