Cesium carbonate → tert-Butyl 1-oxo-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,9-diazaspiro[5.5]undecane-9-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	4-bromo-5H-furan-2-one	HCID 11789536	—
Reactant	tert-Butyl 1-oxo-2,9-diazaspiro[5.5]undecane-9-carboxylate	HCID 49760149	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Product	tert-Butyl 1-oxo-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,9-diazaspiro[5.5]undecane-9-carboxylate	HCID 86709452	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

A microwave vial was charged with commercially available tert-butyl 1-oxo-2,9-diazaspiro[5.5]undecane-9-carboxylate (Shanghai AQ BioPharma Co., Ltd, catalog #ABP3640, 100 mg, 0.373 mmol), 4-bromofuran-2(5H)-one (72.9 mg, 0.447 mmol), Pd2(dba)3 (17.06 mg, 0.019 mmol), Xantphos (32.3 mg, 0.056 mmol), and cesium carbonate (182 mg, 0.559 mmol). The vial was sealed, degassed, and filled with toluene (1.5 mL). The reaction mixture was heated at 90° C. overnight, and was filtered through CELITE®. The filtrate was evaporated to give the crude product, which was purified by column chromatograph (0-10% MeOH/DCM) to afford the title compound. LC/MS: [(M+1-56)]+=295

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08952166B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-9159bd42539d458595b3ea9338674399
Source note	uspto-grants-2015_02