반응 #95822

반응 방정식

ethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate

lithium borohydride

water

hydrochloric acid water

→

8-fluoro-4,5-dihydro-3-(hydroxymethyl)-5-methyl-6H-imidazo[ 1,5-a][1,4]benzodiazepin-6-one

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGstirred at room temperature overnight
2. 2
   기타After removal of the tetrahydrofuran in vacuo
3. 3
   workup.ADDITIONthe residue is treated with 14 ml of concentrated ammonia
4. 4
   workup.WAITThe mixture is left
5. 5
   기타to crystallise in the cold and
6. 6
   기타separated material
7. 7
   여과is filtered off under suction
8. 8
   세척washed with water
9. 9
   기타After recrystallisation from ethanol

실험 절차

15.0 g (49.5 mmol) of ethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate are dissolved under argon in 450 ml of boiling absolute tetrahydrofuran (filtered over Alox) and added dropwise at 50° C. to a solution of 1.1 g (49.5 mmol) of lithium borohydride in 50 ml of absolute tetrahydrofuran. The mixture is stirred at 40° C. for 4 hours and at the boiling point for 2.5 hours. Subsequently, the mixture is decomposed at 40° C. with 20 ml of water and 20 ml of concentrated hydrochloric acid/water (1:1) and stirred at room temperature overnight. After removal of the tetrahydrofuran in vacuo, the residue is treated with 14 ml of concentrated ammonia. The mixture is left to crystallise in the cold and separated material is filtered off under suction and washed with water. After recrystallisation from ethanol, there is obtained 8-fluoro-4,5-dihydro-3-(hydroxymethyl)-5-methyl-6H-imidazo[ 1,5-a][1,4]benzodiazepin-6-one of melting point 221°-223° C.

출처