Nitrogen → tert-Butyl 4-hydroxy-1-oxo-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Nitrogen	HCID 947	—
Reactant	Water	HCID 962	—
Reactant	Potassium Carbonate	HCID 11430	—
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 4-hydroxy-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate	HCID 86709491	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	tert-Butyl 4-hydroxy-1-oxo-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate	HCID 86709498	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

To a round bottom flask was charged tert-butyl 4-hydroxy-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (300 mg, 1.11 mmol), 4-bromofuran-2(5H)-one (271 mg, 1.66 mmol), Pd(OAc)2 (24.9 mg, 0.111 mmol), Xantphos (96 mg, 0.166 mmol), and K2CO3 (307 mg, 2.22 mmol). The flask was sealed, vacuumed and back filled with N2 and filled with dioxane (4.5 mL) and H2O (60.0 μL, 3.33 mmol). The reaction mixture was heated at 90° C. overnight, then filtered through CELITE®, and evaporated to give the crude product, which was purified by column chromatography (0-10% MeOH/DCM) to give the title compound. LC/MS: [(M+1)]+=353

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09206198B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-ecff971837fc4df1aadb402fd5445c62
Source note	uspto-grants-2015_12