Triphenylphosphine → Quinoxaline

HRID 240240

Reaktionsgleichung

Reaktionsgleichung von HRID 240240
O[C@@H:2]1[CH2:6][N:5]([C:7](OC(C)(C)C)=O)[C@H:4]([C:14](OC)=O)[CH2:3]1.[C:18]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:37]([C:45](OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[N:37]1[C:3]2[C:4](=[CH:14][CH:18]=[CH:6][CH:2]=2)[N:5]=[CH:7][CH:45]=1

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl ester

Produkt 1

HCID 7045QuinoxalineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To the solution of 2-9-2 (0.228 g, 0.745 mmol), (2S,4S)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (0.219 g, 0.894 mmol) and Triphenylphosphine (0.293 g, 1.117 mmol) in THF (3.72 ml), the Diisopropyl azodicarboxylate (0.217 ml, 1.117 mmol) was added dropwise at room temperature. The mixture was stirred at room temperature for 2 h. The mixture was concentrated. The crude product was purified by combiflash (25 g silica gel, 0-40% ethyl acetate in Hexanes) to give 1-1-1 (0.320 g, 0.600 mmol, 81% yield). MS-ESI, m/z=534.45 (M+1)+.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customThe crude product was purified by combiflash (25 g silica gel, 0-40% ethyl acetate in Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-4f4ed4ac0bf84b4980af4c7408f0e16c
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648037B2

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