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

HRID 67334

반응식

HRID 67334 반응식
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16](OCC)=[O:17])=[C:5]2[C@@H:4]2[CH2:21][CH2:22][CH2:23][N:3]12.[BH4-].[Li+].Cl>O1CCCC1>[OH:17][CH2:16][C:15]1[N:14]=[CH:13][N:6]2[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:2](=[O:1])[N:3]3[CH2:23][CH2:22][CH2:21][C@H:4]3[C:5]=12

참가 물질

5

반응물 3

HCID 313Hydrochloric Acid2회HCID 4148881Lithium borohydrideHCID 10041121Ethyl (7S)-12-oxo-2,4,11-triazatetracyclo[11.4.0.02,6.07,11]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylate

생성물 1

HCID 54004960(S)-11,12,13,13a-tetrahydro-1-(hydroxymethyl)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 46.7 g (150 mmol) of ethyl (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate in 300 ml of dry tetrahydrofuran is treated dropwise at ca 35° C. with a solution of 8.3 g (377 mmol) of lithium borohydride in 110 ml of dry tetrahydrofuran. The mixture is heated to boiling under reflux for ca 40 hours, cooled to room temperature, treated with 110 ml of 12 percent hydrochloric acid and 20 ml of concentrated hydrochloric acid and again heated to boiling under reflux for 2 hours. After removal of the tetrahydrofuran in vacuo, the residue is made alkaline with concentrated ammonia. The separated material is filtered off under suction and washed with water. After recrystallisation from ethanol, there is obtained (S)-11,12,13,13a-tetrahydro-1-(hydroxymethyl)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 212°-214° C.

후처리

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for ca 40 hours
  3. temperatureagain heated
  4. temperatureunder reflux for 2 hours
  5. customAfter removal of the tetrahydrofuran in vacuo
  6. filtrationThe separated material is filtered off under suction
  7. washwashed with water
  8. customAfter recrystallisation from ethanol

출처 및 근거

ORD 기록
ord-1c3cd4484c2a42c7949080621c95dff8
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04346030

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