聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 8-fluoro-4,5-dihydro-3-(hydroxymethyl)-5-methyl-6H-imidazo [1,5-a][1,4]benzodiazepin-6-one

HRID 67346

反应方程式

HRID 67346 反应方程式
[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

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 3373氟马西尼HCID 4148881硼氢化锂HCID 21885828Hydrate;hydrochloride

产物 1

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

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂2 次

反应条件

温度
40 °C

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-01f48751b0e04f1c933bb4f701c04f98
来源数据集
uspto-grants-1982_08
专利号
US04346031

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