Reaktion #170860

Reaktionsgleichung

5-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)octahydro-1H-pyrrolo[3,4-c]pyridin-1-one

NaH

Benzylbromide

→

title compound

2-benzyl-5-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)octahydro-1H-pyrrolo[3,4-c]pyridin-1-one

Lösungsmittel

DMF

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 18 h under the same conditions
3. 3
   Waschenwashed with 10% aq. sodium carbonate (2×)
4. 4
   Trocknendried with magnesium sulfate
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigePurification
7. 7
   workup.DISSOLUTIONwas dissolved in DCM
8. 8
   Sonstigerapid solvent removal

Vorschrift

5-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)octahydro-1H-pyrrolo[3,4-c]pyridin-1-one (64 mg, 0.245 mmol) was dissolved in anhydrous DMF (5 mL). NaH (60% oil suspension, 29 mg, 0.735 mmol) was added at rt under nitrogen and stirred for 1 h. Benzylbromide (0.035 mL, 0.294 mmol) was added and stirring continued for 18 h under the same conditions. After this time, the solution was diluted with ethyl acetate and washed with 10% aq. sodium carbonate (2×), dried with magnesium sulfate, and concentrated in vacuo. Purification was done via silica gel flash chromatography (25 g silica, 80% EtOAc/hexanes.) The residue was dissolved in DCM, and rapid solvent removal afforded the title compound as a white powder. (Yield: 56 mg, 0.112 mmol, 72%) 1H NMR (400 MHz, CDCl3) 7.69, 7.33-6.99, 5.47, 4.56, 4.38, 4.11, 3.39-3.36, 2.94-2.82, 2.53-2.47, 1.75, 1.39

Quelle