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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1501801Generated: November 2, 2026

1,8-Diazabicyclo(5.4.0)undec-7-ene → tert-Butyl 2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]dec-3-ene-8-carboxylate

https://huagongshe.com/reaction/1501801

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
Reactant(Diethylamino)(difluoro)sulfanium tetrafluoroborateHCID 44517918—
Reactanttert-Butyl 4-hydroxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylateHCID 86709492—
SolventDichloromethaneHCID 6344—
Producttert-Butyl 2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]dec-3-ene-8-carboxylateHCID 86709496—

Reaction Steps

To a solution of tert-butyl 4-hydroxy-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (300 mg, 0.819 mmol) in DCM (8.2 mL) at 0° C. was added DBU (370 μA, 2.46 mmol), and XtalFluor-E® (562 mg, 2.46 mmol). The mixture was stirred overnight while warming up to rt, and quenched with aqueous NaHCO3. The organic layer was separated and the aqueous layer was extracted with DCM (30 mL). The combined organic layers were dried (MgSO4) and purified by column chromatography (0-100% EtOAc/hex) to give the title compound. LC/MS: [(M+1)]+=349

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09206198B2
Source datasetuspto-grants-2015_12
ORD IDord-10dd98384937409ca2e08829a8301a6f
Source noteuspto-grants-2015_12