Dimethylformamide → Methyl 3-[4-(N-BOC-Piperidin-4-yl)butyloxy]isoxazole-5-carboxylate

HRID 1957581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1957581
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17]I)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])([O-])=O.[Cs+].[Cs+].[OH:25][C:26]1[CH:30]=[C:29]([C:31]([O:33][CH3:34])=[O:32])[O:28][N:27]=1.CN(C=O)C>CCOCC>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][O:25][C:26]2[CH:30]=[C:29]([C:31]([O:33][CH3:34])=[O:32])[O:28][N:27]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 193480344-(N-BOC-Piperidin-4-yl)butyl iodideHCID 178498603HCID 178498603, Verbindung

Produkt 1

HCID 19068162Methyl 3-[4-(N-BOC-Piperidin-4-yl)butyloxy]isoxazole-5-carboxylateAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 4-3 (3.0 g, 8.1 mmol), Cs2CO3 (2.6 g, 8.1 mmol), methyl 3-hydroxy-5-isoxazolecarboxylate (Aldrich) (1.2 g, 8.1 mmol), and DMF (20 mL) was stirred at ambient temperature for 20 h. The reaction mixture was diluted with ether and then washed with H2O and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 3% acetone/CH2Cl2) gave 4-4 (2.7 g) as a colorless solid. Rf 0.17 (silica, 3% acetone/CH2Cl2).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-41880a4de2224318be61d23dfce8a42d
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05786373

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