Triphenylphosphine → (S)-1-benzyl-3-ethylpiperazine-2-one

HRID 249874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 249874
[NH2:1][C@@H:2]([CH2:16][CH3:17])[C:3]([N:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][CH2:7]O)=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:9]([N:5]1[CH2:6][CH2:7][NH:1][C@@H:2]([CH2:16][CH3:17])[C:3]1=[O:4])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

4

Edukt 2

HCID 11776TriphenylphosphineHCID 66874126(S)-2-amino-N-benzyl-N-(2-hydroxyethyl)butanamide

Produkt 1

HCID 45095306(S)-1-benzyl-3-ethylpiperazine-2-oneAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Diisopropylazidodicarboxylate (1.82 g, 9.3 mmol) was added to solution of (S)-2-amino-N-benzyl-N-(2-hydroxyethyl)butanamide (1.84 g, 7.8 mmol) and triphenylphosphine (2.62 g, 10.0 mmol) in THF (50 mL). The reaction mixture was stirred at room temperature for 7 d. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (silica gel, 10% CH3OH in EtOAc) to afford (S)-1-benzyl-3-ethylpiperazine-2-one (0.8 g, 47%) as clear oil. 1H NMR consistent.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography (silica gel, 10% CH3OH in EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-729d3d4d430a4bb685c6c1aadc70cc45
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863271B2

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