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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 627248Generated: November 2, 2026

(S,E)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-yl(2-oxopent-3-enyl)carbamate → (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-cyclopropyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

https://huagongshe.com/reaction/627248

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(S,E)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-yl(2-oxopent-3-enyl)carbamateHCID 89851850—
Reactanttert-Butyl (6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-4-methyl-3-oxo-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 89852373—
Product(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-cyclopropyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylateHCID 89851848—

Reaction Conditions

Temperature110 °C

Reaction Steps

The title compound was prepared from (S,E)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-yl(2-oxopent-3-enyl)carbamate (Intermediate 236, 4 g, 9.44 mmol) following the procedure described for Intermediate 7, except the reaction mixture was heated at 110° C. overnight. The desired product was obtained as a light brown oil (2.97 g, 82%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09309245B2
Source datasetuspto-grants-2016_04
ORD IDord-779babc490194b6c968d5554fcfa78ca
Source noteuspto-grants-2016_04