Trifluoroacetic acid → rac-cis-1,3,3a,4,5,9b-hexahydro-6-methoxy-2H-benzo[e]indol-2-one

HRID 1109093노트

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HRID 1109093 반응식
[CH3:1][O:2][C:3]1[C:15]2[CH2:14][CH2:13][C:12]3[NH:11][C:10](=[O:16])[CH2:9][C:8]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl.O>[CH3:1][O:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][C:10](=[O:16])[NH:11]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 190214751,3,4,5-tetrahydro-6-methoxy-2H-benzo[e]indol-2-one

생성물 1

HCID 131718423rac-cis-1,3,3a,4,5,9b-hexahydro-6-methoxy-2H-benzo[e]indol-2-one수율 67%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

313 g (1.45 mol) of 1,3,4,5-tetrahydro-6-methoxy-2H-benzo[e]indol-2-one were suspended in 3 l of methylene chloride. After the addition of 690 ml (4.33 mol) of triethylsilane 500 ml (6.53 mol) of trifluoroacetic acid were slowly added dropwise at 0°, whereupon the mixture was stirred at room temperature for 3 hours, then cooled with an ice-ethanol bath, made alkaline with about 830 ml of 28% sodium hydroxide solution, poured into water and extracted with methylene chloride. The organic phase was washed with saturated sodium chloride solution and dried with sodium sulphate. After distillation of the solvent in a vacuum the residue was suspended in ice-cold ether. The solid was filtered off, rinsed with ether and dried. There were obtained 210 g (67%) of rac-cis-1,3,3a,4,5,9b-hexahydro-6-methoxy-2H-benzo[e]indol-2-one as white crystals with m.p. 192°-194°.

후처리

  1. additionwere slowly added dropwise at 0°, whereupon the mixture
  2. temperaturecooled with an ice-ethanol bath
  3. extractionextracted with methylene chloride
  4. washThe organic phase was washed with saturated sodium chloride solution
  5. dry with materialdried with sodium sulphate
  6. distillationAfter distillation of the solvent in a vacuum the residue
  7. filtrationThe solid was filtered off
  8. washrinsed with ether
  9. customdried

출처 및 근거

ORD 기록
ord-1914a9c09597489291923c2eb4301ed2
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05318966

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