(Triphenylphosphoranylidene)acetonitrile → HCID 86596606, Verbindung

HRID 133822

Reaktionsgleichung

Reaktionsgleichung von HRID 133822
[CH:1]([C@@H:3]([N:7]([CH3:15])[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:4]([CH3:6])[CH3:5])=O.C1(P(=[CH:35][C:36]#[N:37])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:36](/[CH:35]=[CH:1]/[C@@H:3]([N:7]([CH3:15])[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:4]([CH3:6])[CH3:5])#[N:37]

Komponenten

4

Edukt 2

HCID 85524(Triphenylphosphoranylidene)acetonitrile2×HCID 10353241tert-butyl (1S)-1-formyl-2-methylpropyl(methyl)carbamate

Produkt 1

HCID 86596606HCID 86596606, VerbindungAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (1S)-1-formyl-2-methylpropyl(methyl)carbamate (WO 99/32509) (500 mg, 202 mmol) in dicloromethane (5 mL) is added (triphenylphosphoranylidene)acetonitrile (700 mg, 2.32 mmol). After 1 h additional (triphenylphosphoranylidene)acetonitrile is added (350 mg, 1.16 mmol). After 24 h the reaction mixture is concentrated in vacuo and chromatographed (silica gel, hexane/ether) to give the title compound as an oil (410 mg). Analysis for C13H22N2O2: Calc'd: C, 65.52; H, 9.3; N 11.75. Found: C, 65.3; H, 9.05; N,11.51. MS (ES): m/z 239.1 (M+H)

Aufarbeitung

  1. concentrationAfter 24 h the reaction mixture is concentrated in vacuo
  2. customchromatographed (silica gel, hexane/ether)

Quellen und Nachweise

ORD-Eintrag
ord-a9e8d4309b7842ac9848f80fb25caf0b
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390910B2

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