Triethylamine → (S)-1-(2-azido-propyl)-7-fluoro-1,4-dihydro-indeno[1,2-b]pyrrole

1.17 ml of methanesulfonyl chloride were added dropwise while stirring to a solution, cooled to 0°, of 1.73 g of (R)-1-(7-fluoro-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol and 4.2 ml of triethyl-amine in 60 ml of dichloromethane and the mixture was stirred at this temperature for an additional 1.5 hours. The reaction mixture was subsequently diluted with 150 ml of diethyl ether, washed twice with 60 ml of saturated sodium hydrogen carbonate solution each time and the combined aqueous phases were extracted once with 70 ml of diethyl ether. The combined organic phases were washed with 70 ml of saturated sodium chloride solution, dried over magnesium sulfate and evaporated in a vacuum. The brown oil obtained was dissolved in 50 ml of anhydrous dimethylformamide, treated with 973 mg of sodium azide and the reaction mixture was heated to 50° for 15 hours while stirring. After cooling, the solution was poured into 110 ml of water and extracted twice with 110 ml of diethyl ether each time and once with 60 ml of ethyl acetate. The combined organic phases were washed once with 80 ml of water and once with 80 ml of saturated sodium chloride solution, dried over magnesium sulfate and the solution was concentrated in a vacuum. The brown oil obtained was purified by column chromatography on silica gel (toluene). 750 mg (39%) of (S)-1-(2-azido-propyl)-7-fluoro-1,4-dihydro-indeno[1,2-b]pyrrole were obtained as a colorless oil.

1. stirringthe mixture was stirred at this temperature for an additional 1.5 hours
2. washwashed twice with 60 ml of saturated sodium hydrogen carbonate solution each time
3. extractionthe combined aqueous phases were extracted once with 70 ml of diethyl ether
4. washThe combined organic phases were washed with 70 ml of saturated sodium chloride solution
5. dry with materialdried over magnesium sulfate
6. customevaporated in a vacuum
7. customThe brown oil obtained
8. temperaturethe reaction mixture was heated to 50° for 15 hours
9. stirringwhile stirring
10. temperatureAfter cooling
11. extractionextracted twice with 110 ml of diethyl ether each time
12. washThe combined organic phases were washed once with 80 ml of water and once with 80 ml of saturated sodium chloride solution
13. dry with materialdried over magnesium sulfate
14. concentrationthe solution was concentrated in a vacuum
15. customThe brown oil obtained
16. customwas purified by column chromatography on silica gel (toluene)

ORD-Eintrag

ord-64e94a1a2ebd48658e4cc8cf34d9282f

Quelldatensatz

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05646173