Sodium Bicarbonate → cis-3-(6-Methoxypyridin-3-yl) 3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

HRID 600720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600720
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:5]=[N:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=1.[C:13]([N:20]1[CH2:24][CH2:23][CH:22]=[CH:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[C:16]([O:15][C:13]([N:20]1[CH2:24][C@H:23]2[C@H:22]([C:3]([C:4]3[CH:5]=[N:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=3)=[N:2][O:1]2)[CH2:21]1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 10844857tert-Butyl 2,3-dihydro-1H-pyrrole-1-carboxylateHCID 76564447N-Hydroxy-6-methoxy-3-pyridinecarboximidoyl chloride

Produkt 1

HCID 68971835cis-3-(6-Methoxypyridin-3-yl) 3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

Chloro oxime 2c (1.12 g; 5.99 mmol), N-Boc-pyrroline (0.5 mL; 2.90 mmol) and sodium bicarbonate (0.61 g) in ethyl acetate (40 mL) were stirred at room temperature for 24 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried (MgSO4), filtered and evaporated to yield crude cycloadduct. 3c was isolated as a white solid after chromatography with 25% ethyl acetate/hexanes.

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto yield crude cycloadduct

Quellen und Nachweise

ORD-Eintrag
ord-2f035dffe65f4a80ae0715be7fe1d85d
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902227B2

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