Water → rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole

HRID 1109094노트

반응식

HRID 1109094 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:21]2[CH2:20][CH2:19][C@H:18]3[C@H:14]([CH2:15][C:16](=O)[NH:17]3)[C:13]=2[CH:12]=[CH:11][CH:10]=1.O.[OH-].[Na+]>O1CCCC1>[CH3:7][O:8][C:9]1[C:21]2[CH2:20][CH2:19][C@H:18]3[C@H:14]([CH2:15][CH2:16][NH:17]3)[C:13]=2[CH:12]=[CH:11][CH:10]=1

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 131718423rac-cis-1,3,3a,4,5,9b-hexahydro-6-methoxy-2H-benzo[e]indol-2-one

생성물 1

HCID 101650127rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole수율 96%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A suspension of 25 g (0.66 mol) of lithium aluminum hydride in 2 l of tetrahydrofuran was treated portionwise with 71.5 g (0.33 mol) of rac-cis-1,3,3a,4,5,9b-hexahydro-6-methoxy-2H-benzo[e]indol-2-one. The mixture was boiled at reflux overnight, cooled to about -10° and then hydrolyzed by the successive dropwise addition of 25 ml of water, 25 ml of 15 percent sodium hydroxide solution and 75 ml of water. The solid residue was filtered off and rinsed with methylene chloride. The organic phases were concentrated. The residue was dissolved in methylene chloride and the solution was dried with sodium sulphate. After distillation of the solvent in a vacuum and crystallization in a refrigerator there were obtained 64.0 g (96%) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole as grey crystals.

후처리

  1. temperatureat reflux overnight
  2. temperaturecooled to about -10°
  3. filtrationThe solid residue was filtered off
  4. washrinsed with methylene chloride
  5. concentrationThe organic phases were concentrated
  6. dissolutionThe residue was dissolved in methylene chloride
  7. dry with materialthe solution was dried with sodium sulphate
  8. distillationAfter distillation of the solvent
  9. customin a vacuum and crystallization in a refrigerator

출처 및 근거

ORD 기록
ord-c9156b5583a4473c865705311969da26
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05318966

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