Reaktion #3773

Reaktionsgleichung

water

(S)-7-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,6,7,8,12b-hexahydro-6-oxopyrido[2,1-a][2]benzazepine

sulfuric acid

formic acid

→

title compound

(S)-7-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,3,4,6,7,8,12b-octahydro-6-oxopyrido[2,1-a][2]benzazepine-4-carboxylic acid

Lösungsmittel

ethyl acetate hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequickly seal the vessel
2. 2
   ExtraktionExtract the reaction mixture with ethyl acetate
3. 3
   ExtraktionExtract the organic layer with saturated aqueous potassium carbonate solution (5×10 mL)
4. 4
   ExtraktionExtract with chloroform (5×15 mL)
5. 5
   TrocknenCombine the organic layers, dry over MgSO4
6. 6
   Filtrationfilter
7. 7
   Sonstigeevaporate in vacuo
8. 8
   Sonstigeto give a residue

Vorschrift

Combine (S)-7-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,6,7,8,12b-hexahydro-6-oxopyrido[2,1-a][2]benzazepine (32 mg, 0.09 mmol) and sulfuric acid (1.0 mL, 95-98%) in a pressure vessel. Add 96% formic acid (200 μL) and quickly seal the vessel. After 18 hours, add water (10 mL). Extract the reaction mixture with ethyl acetate. Extract the organic layer with saturated aqueous potassium carbonate solution (5×10 mL). Combine the aqueous layers and carefully acidify with aqueous 12M hydrochloric acid solution. Extract with chloroform (5×15 mL). Combine the organic layers, dry over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 2/1 ethyl acetate/hexane containing 0.5% acetic acid to give the title compound. Rf =0.14 (silica gel, 2/1 ethyl acetate/hexane containing 0.5% acetic acid).

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