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

HRID 2045725Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2045725
[Cl:1][C:2]1[C:3]([OH:12])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.O[C@@H:14]1[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:16]([C:26]([O:28][CH3:29])=[O:27])[CH2:15]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[C:3]([O:12][C@H:14]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:16]([C:26]([O:28][CH3:29])=[O:27])[CH2:15]2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 3027053-chloro-1H-quinoxalin-2-oneHCID 5363146Diisopropyl azodicarboxylateHCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl ester

Produkt 1

HCID 580914191-t-Butyl 2-methyl (2S,4R)-4-[(3-chloroquinoxalin-2-yl)oxy]pyrrolidine-1,2-dicarboxylateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

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)+.

Aufarbeitung

  1. customAfter evaporation of the volatiles
  2. customthe residue was purified on silica gel (gradient elution, 0-70% EtOAc/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-c5e941b6d7d04d40a8ecb5e7030d2752
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08591878B2

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