Propargyl bromide → tert-Butyl 16-oxo-15-prop-2-yn-1-yl-6,15-diazadispiro[4.2.6.2]hexadecane-6-carboxylate

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Reaction Steps

Sodium hydride (23 mg, 0.575 mmol, 60% dispersion in mineral oil) was added to a stirred solution of tert-butyl 16-oxo-6,15-diazadispiro[4.2.6.2]hexadecane-6-carboxylate from Step A (92 mg, 0.273 mmol) in DMF (1 mL). When the gas evolution had ceased, propargyl bromide (70 mg, 0.471 mmol, 80 wt % in toluene) was added to the solution at ambient temperature. After 1 h, the reaction was quenched with water (30 mL) and extracted with EtOAc (30 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to yield the title compound. MS: m/z=397 (M+Na).

Provenance & Evidence