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

HRID 67395

반응식

HRID 67395 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15](OCC)=[O:16])=[C:10]3[CH2:9][N:8]([CH3:20])[C:7](=[O:21])[C:6]=2[CH:22]=1.[BH4-].[Li+].O.Cl.O>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([CH2:15][OH:16])=[C:10]3[CH2:9][N:8]([CH3:20])[C:7](=[O:21])[C:6]=2[CH:22]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 3373FlumazenilHCID 4148881Lithium borohydrideHCID 21885828Hydrate;hydrochloride

생성물 1

HCID 205153408-fluoro-4,5-dihydro-3-(hydroxymethyl)-5-methyl-6H-imidazo [1,5-a][1,4]benzodiazepin-6-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
40 °C

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.

후처리

  1. stirringstirred at room temperature overnight
  2. customAfter removal of the tetrahydrofuran in vacuo
  3. additionthe residue is treated with 14 ml of concentrated ammonia
  4. waitThe mixture is left
  5. customto crystallise in the cold and
  6. customseparated material
  7. filtrationis filtered off under suction
  8. washwashed with water
  9. customAfter recrystallisation from ethanol

출처 및 근거

ORD 기록
ord-680e5911004e401295dc2ce33b0e6107
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04346032

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