Triphenylphosphine → Methyl 5-bromo-6-oxo-1-(3-phenylcyclopentyl)-1,6-dihydropyridine-3-carboxylate

HRID 253091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 253091
[Br:1][C:2]1[C:7](=[O:8])[NH:6][CH:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1.[C:13]1([CH:19]2[CH2:23][CH2:22][CH:21](O)[CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C(OC(=O)C)C>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH:22]2[CH2:21][CH2:20][CH:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:23]2)[CH:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2756203-Phenylcyclopentan-1-olHCID 2764315Methyl 5-bromo-6-hydroxynicotinate

Produkt 1

HCID 66844665Methyl 5-bromo-6-oxo-1-(3-phenylcyclopentyl)-1,6-dihydropyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of methyl 5-bromo-6-oxo-1,6-dihydropyridine-3-carboxylate (1.6 g, 6.8 mmol), 3-phenylcyclopentanol (1.32 g, 8.15 mmol) and triphenylphosphine (2.7 g, 10.2 mmol) in dry THF (15 mL) was slowly added diethyl azodicarboxylate (1.8 g, 10.2 mmol) at RT. The resulting yellow solution was stirred at room temperature for 17 h. The mixture was diluted in ethylacetate, washed with water, brine, dried over MgSO4, and chromatographed on silica gel using hexanes to 3:1 hexanes:ethylacetate, to afford the title compound. MS m/z: 376 (M+1).

Aufarbeitung

  1. customat RT
  2. washwashed with water, brine
  3. dry with materialdried over MgSO4
  4. customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-23391fb9e5f04c8db0331fa34b411ec5
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872009B2

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