Reaction #170859

Reaction equation

HOBT

1-(4-chlorobenzyl)-1H-indole-2-carboxylic acid

DIPEA

octahydro-1H-pyrrolo[3,4-c]pyridin-1-one

EDC

→

title compound

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

Solvents

DMF

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Otherthe solution was partitioned between water and 1:1 solution of ethyl acetate
3. 3
   ExtractionThe organic extract
4. 4
   Washwas then washed with water (1×) and saturated aq. sodium carbonate (1×)
5. 5
   Dryingdried with magnesium sulfate
6. 6
   Concentrationconcentrated in vacuo
7. 7
   OtherPurification
8. 8
   OtherResulting residue
9. 9
   Otherwas crystallized from the
10. 10
    Otherin vacuo removal of DCM

Procedure

The following was added sequentially to DMF (10 mL): 1-(4-chlorobenzyl)-1H-indole-2-carboxylic acid (250 mg, 0.875 mmol), DIPEA (0.46 mL, 2.64 mmol), EDC (202 mg, 1.050 mmol), and HOBT (162 mg, 1.050 mmol). This solution was allowed to stir at rt for 1 h, at which time crude octahydro-1H-pyrrolo[3,4-c]pyridin-1-one (˜123 mg, 0.875 mmol) was added. Stirring continued for 12 h at rt, at which time the solution was partitioned between water and 1:1 solution of ethyl acetate:diethyl ether. The organic extract was then washed with water (1×) and saturated aq. sodium carbonate (1×), dried with magnesium sulfate, and concentrated in vacuo. Purification was accomplished via silica gel flash chromatography (100 g silica, 100% EtOAc.) Resulting residue was crystallized from the in vacuo removal of DCM to give the title compound as a slightly pink solid. (Yield: 200 mg, 0.49 mmol, 56%) 1H NMR (400 MHz, CDCl3) 7.72, 7.40-7.24, 7.20, 7.17-7.11, 6.94, 6.31, 5.51, 4.57, 4.30-4.08, 3.59-3.46, 3.39, 3.17-3.02, 2.63, 2.51, 2.02-1.77

Source