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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 627127Erstellt: 25. Oktober 2026

Tetrabutylammonium Fluoride → (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(hydroxymethyl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxylate

https://huagongshe.com/reaction/627127

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTetrabutylammonium FluorideHCID 2724141—
Edukt(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxylateHCID 89852556—
LösungsmittelTetrahydrofuranHCID 8028—
Produkt(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(hydroxymethyl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxylateHCID 8985240779,3%

Reaktionsschritte

(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 80, 7.05 g, 11.79 mmol) in THF (100 mL) was charged with nitrogen and cooled in an ice-bath. Tetrabutylammonium fluoride in THF (14.15 mL, 14.15 mmol) was added to the solution and stirred at rt. The reaction mixture was evaporated and the crude product was loaded onto silica and purified via flash chromatography (30-100% EA/Hexanes, 40 g column), to obtain the desired product (4.52 g, 79%) as a pale yellow foam.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09309245B2
Quelldatensatzuspto-grants-2016_04
ORD IDord-a9fae5c93a9a42e2882c69ddbe1f682e
Quellennotizuspto-grants-2016_04