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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 2045725Erstellt: 27. Oktober 2026

Triphenylphosphine → 1-t-Butyl 2-methyl (2S,4R)-4-[(3-chloroquinoxalin-2-yl)oxy]pyrrolidine-1,2-dicarboxylate

https://huagongshe.com/reaction/2045725

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTriphenylphosphineHCID 11776—
Edukt3-chloro-1H-quinoxalin-2-oneHCID 302705—
EduktDiisopropyl azodicarboxylateHCID 5363146—
EduktN-Boc-cis-4-hydroxy-L-proline methyl esterHCID 10752873—
LösungsmittelTetrahydrofuranHCID 8028—
Produkt1-t-Butyl 2-methyl (2S,4R)-4-[(3-chloroquinoxalin-2-yl)oxy]pyrrolidine-1,2-dicarboxylateHCID 5809141977%

Reaktionsbedingungen

Temperatur20 °C

Reaktionsschritte

A solution of 3-chloroquinoxalin-2-ol (1.44 g, 7.97 mmol) and 1-tert-butyl 2-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate (2.05 g, 8.37 mmol) in THF (190 ml) was cooled to 0° C., then treated with PPh3 (2.51 g, 9.57 mmol). DIAD (1.86 ml, 9.57 mmol) was added dropwise, and the mixture was stirred at 20° C. for 1 h. After evaporation of the volatiles, the residue was purified on silica gel (gradient elution, 0-70% EtOAc/petroleum ether) to afford the title compound (2.5 g, 77%). LCMS (ES+) m/z 408 (M+H)+.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08591878B2
Quelldatensatzuspto-grants-2013_11
ORD IDord-c5e941b6d7d04d40a8ecb5e7030d2752
Quellennotizuspto-grants-2013_11