Dimethylformamide → HCID 19068171, Verbindung

HRID 1957576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1957576
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1.[C:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH2:26]I)[CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>CCOCC>[C:11]([N:18]1[CH2:19][CH2:20][CH:21]([CH2:24][CH2:25][CH2:26][O:1][C:2]2[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=2)[CH2:22][CH2:23]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 9975355Tert-butyl 4-(3-iodopropyl)piperidine-1-carboxylateHCID 178498603HCID 178498603, Verbindung

Produkt 1

HCID 19068171HCID 19068171, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of methyl 3-hydroxy-5-isoxazolecarboxylate (Aldrich) (3-5) (286 mg, 2.0 mmol), 3-4 (706 mg, 2.0 mmol), Cs2CO3 (650 mg, 2.0 mmol), and DMF (10 mL) was stirred at ambient temperature. After 72 hours the reaction mixture was diluted with ether and then washed with H2O and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 4% acetone/CH2Cl2) gave 3-6 as a colorless solid. Rf 0.54 (silica, 40 %EtOAc/hexanes).

Aufarbeitung

  1. washwashed with H2O and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-18110f652a764c16bd5b52672752c62f
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05786373

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