Methyl morpholine oxide → 1-(3-Methoxymethoxy-2-oxo-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile

HRID 1672503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1672503
[OH:1][CH:2]([CH:24]([O:26][CH2:27][O:28][CH3:29])[CH3:25])[CH2:3][N:4]1[C:9]([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=[CH:8][C:7]([C:17]([F:20])([F:19])[F:18])=[C:6]([C:21]#[N:22])[C:5]1=[O:23].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:29][O:28][CH2:27][O:26][CH:24]([CH3:25])[C:2](=[O:1])[CH2:3][N:4]1[C:9]([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=[CH:8][C:7]([C:17]([F:18])([F:19])[F:20])=[C:6]([C:21]#[N:22])[C:5]1=[O:23]

Komponenten

5

Edukt 2

HCID 82029Methyl morpholine oxideHCID 673389801-(2-Hydroxy-3-methoxymethoxy-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile

Produkt 1

HCID 673402801-(3-Methoxymethoxy-2-oxo-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrileAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419074HCID 178419074, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-(2-Hydroxy-3-methoxymethoxy-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile 29 (0.21 g, 0.52 mmoles) was combined with N-methylmorpholine N-oxide (NMO, 92 mg, 0.79 mmoles) and 4 Å molecular sieves (powder, 170 mg) in 5 mL of anhydrous DCM within a 7 mL reaction vial. The mixture was stirred at room temperature for 10 min. After this period tetrapropylammonium perruthenate (TPAP, 10 mg, 0.028 mmoles) was added and the mixture was stirred at room temperature for an additional 3 hours. After this period the reaction mixture was purified directly using flash silica chromatography (0-40% EtOAc/Hexane) to yield 0.191 g (90% yield) of 1-(3-Methoxymethoxy-2-oxo-butyl)-2-oxo-6-m-tolyl-4-trifluoromethyl-1,2-dihydro-pyridine-3-carbonitrile as a yellow residue.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for an additional 3 hours
  2. customAfter this period the reaction mixture was purified directly

Quellen und Nachweise

ORD-Eintrag
ord-aea83a1d4c4c483da26a634eea95f117
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998986B2

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