Hydrochloric Acid → (S)-8-chloro-11,12,13,13a-tetrahydro-1-(hydroxymethy)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one

HRID 867537ノート

反応式

HRID 867537 の反応式
[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]3[CH2:23][CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](OCC)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].Cl.O>O1CCCC1>[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]3[CH2:23][CH2:22][CH2:21][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[CH2:16][OH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric Acid2 回HCID 962WaterHCID 4148881Lithium borohydrideHCID 53890667ethyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepine-1-carboxylate

生成物 1

HCID 54098055(S)-8-chloro-11,12,13,13a-tetrahydro-1-(hydroxymethy)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A suspension of 81.2 g (234.8 mmol) of ethyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate in 450 ml of dry tetrahydrofuran is heated to about 50° and a suspension of 6.1 g (279 mmol) of lithium borohydride in 60 ml of tetrahydrofuran is added dropwise to the solution obtained. The suspension is subsequently heated to boiling under reflux for 3 hour. The mixture is cooled to room temperature and there are added dropwise thereto firstly 40 ml of 3N hydrochloric acid and then 260 ml of a solution consisting of 130 ml of conc. hydrochloric acid and 130 ml of water. The solution obtained is stirred at 40° for 15 minutes, the tetrahydrofuran is distilled off in vacuo and the aqueous residue is made alkaline with 25 percent ammonia. The precipitated material is then filtered off under suction, washed with water and dried at 80° in high vacuum. There is obtained (S)-8-chloro-11,12,13,13a-tetrahydro-1-(hydroxymethy)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 303°-305° .

後処理

  1. temperatureis heated to about 50°
  2. additionis added dropwise to the solution
  3. customobtained
  4. temperatureThe suspension is subsequently heated
  5. temperatureunder reflux for 3 hour
  6. additionthere are added dropwise
  7. customThe solution obtained
  8. distillationthe tetrahydrofuran is distilled off in vacuo
  9. filtrationThe precipitated material is then filtered off under suction
  10. washwashed with water
  11. customdried at 80° in high vacuum

出典と根拠

ORDレコード
ord-5b1c6cc3b06b42cd8e302d12635f97fb
出典データセット
uspto-grants-1988_10
特許番号
US04775671

反応ノート

読み込み中…