Reaction #1328411

Reaction equation

(S)-7-benzyloxy-3-(3-iodo-2-phthalimidopropyl)indole

potassium carbonate

ammonium formate

→

title compound

Yield 79.4%

(R)-7-benzyloxy-3-(2-phthalimidopropyl)indole

Yield 79.4%

Solvents

DMF

Conditions

Workup

1. 1
   workup.ADDITIONAdded
2. 2
   TemperatureAfter cooling down
3. 3
   Filtrationthe catalyst was filtered off
4. 4
   workup.ADDITIONthe filtrate was diluted with ethyl acetate
5. 5
   workup.ADDITIONThen, water was added
6. 6
   Otherthe organic layer was separated
7. 7
   WashThe organic layer was washed in order with a 10% sodium thiosulfate aqueous solution
8. 8
   Dryinga sodium hydroxide aqueous solution, hydrochloric acid and a saturated sodium chloride aqueous solution, and then it was dried
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated under reduced pressure

Procedure

A 10% palladium on carbon catalyst (content 50%) 4.00 g was suspended in 200 ml of DMF, and 20.00 g of (S)-7-benzyloxy-3-(3-iodo-2-phthalimidopropyl)indole was added thereto. Added while stirring were 8.00 g of potassium carbonate and 6.00 g of ammonium formate, the suspension was heated in an oil bath of 85° C. For one hour. After cooling down, the catalyst was filtered off, and the filtrate was diluted with ethyl acetate. Then, water was added thereto, and the organic layer was separated. The organic layer was washed in order with a 10% sodium thiosulfate aqueous solution, a sodium hydroxide aqueous solution, hydrochloric acid and a saturated sodium chloride aqueous solution, and then it was dried, filtered and concentrated under reduced pressure, whereby 12.16 g of the title compound was obtained in the form of a yellow amorphous solid shaped substance.

Source