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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1478015Generated: October 31, 2026

Methyl vinyl ketone → Tert-butyl 9-oxo-3-azaspiro[5.5]undec-7-ene-3-carboxylate

https://huagongshe.com/reaction/1478015

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl vinyl ketoneHCID 6570—
ReactantPotassium HydroxideHCID 14797—
Reactanttert-Butyl 4-formylpiperidine-1-carboxylateHCID 1514430—
SolventEthanolHCID 702—
ProductTert-butyl 9-oxo-3-azaspiro[5.5]undec-7-ene-3-carboxylateHCID 5931181741.8%

Reaction Conditions

Temperature70 °C

Reaction Steps

To a solution of tert-butyl 4-formylpiperidine-1-carboxylate (10.0 g, 46.9 mmol) and KOH (1.3 g, 23.5 mmol) in EtOH (200 mL) was added but-3-en-2-one (3.9 g, 56.3 mmol), the mixture was stirred at 70° C. for 16 h and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/4) to give the product as brown oil (5.2 g, 41.8%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09403801B2
Source datasetuspto-grants-2016_08
ORD IDord-3e28273dfecd43d08e8928ea5048caa7
Source noteuspto-grants-2016_08