反応 #1889993

反応方程式

sodium hydroxide

Ethyl 7-nitroindole-2-carboxylate

tetrahydro-4H-pyran-4-one

sodium triacetoxyborohydride

hydrochloric acid

→

title compound

収率 76.0%

7-(tetrahydro-pyran-4-ylamino)-1H-indole-2-carboxylic acid

収率 76.0%

溶媒

tetrahydrofuran

water

methanol

1,2-dichloroethane

反応条件

後処理

1. 1
   ろ過The mixture was filtered though celite
2. 2
   workup.DISTILLATIONthe filtrate was distilled under reduced pressure
3. 3
   workup.ADDITIONwere added
4. 4
   workup.STIRRINGThe mixture was stirred for 8 h at room temperature
5. 5
   workup.ADDITIONwas added
6. 6
   抽出The mixture was extracted with ethyl acetate
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   ろ過filtered
9. 9
   workup.DISTILLATIONThe filtrate was distilled under reduced pressure
10. 10
    濃縮concentrated
11. 11
    その他The residue was purified by column chromatography
12. 12
    workup.DISSOLUTIONThus obtained compound was dissolved in methanol (50 ml)
13. 13
    workup.STIRRINGthe mixture was stirred for 8 h at room temperature
14. 14
    抽出the mixture was extracted with ethyl acetate
15. 15
    乾燥dried over anhydrous magnesium sulfate
16. 16
    ろ過filtered
17. 17
    workup.DISTILLATIONThe filtrate was distilled under reduced pressure

実験手順

Ethyl 7-nitroindole-2-carboxylate (2.5 g, 10.7 mmol) was dissolved in methanol (50 ml). 10% Pd/C (200 mg) was added, and the mixture was stirred for 1 h under hydrogen gas. The mixture was filtered though celite, and the filtrate was distilled under reduced pressure. The distillate was dissolved 1,2-dichloroethane (50 ml), and tetrahydro-4H-pyran-4-one (1.3 ml, 12.8 mmol) and sodium triacetoxyborohydride (3.4 g, 16.1 mmol) were added. The mixture was stirred for 8 h at room temperature. After completion of the reaction, water was added. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure and concentrated. The residue was purified by column chromatography. Thus obtained compound was dissolved in methanol (50 ml) and tetrahydrofuran (50 ml), 1N-sodium hydroxide (43 ml, 42.8 mmol) was added, and the mixture was stirred for 8 h at room temperature. 1N-hydrochloric acid solution was added, and the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled under reduced pressure to give the title compound (2.1 g, Yield 76%).

出典