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Hydrochloric Acid → rac-cis-3-(2-cyclopentyl-ethyl)-6-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indole hydrochloride

HRID 1109197
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HRID 1109197 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:12][C:13]([N:15]2[C@@H:23]3[C@@H:18]([C:19]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[C:20]=4[CH2:21][CH2:22]3)[CH2:17][CH2:16]2)=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-].[Na+].[ClH:32]>C1COCC1.C(O)C.O.C1COCC1.O>[ClH:32].[CH:7]1([CH2:12][CH2:13][N:15]2[C@@H:23]3[C@@H:18]([C:19]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[C:20]=4[CH2:21][CH2:22]3)[CH2:17][CH2:16]2)[CH2:11][CH2:10][CH2:9][CH2:8]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 131718458rac-cis-3-(cyclopentylacetyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole

생성물 1

HCID 131718459rac-cis-3-(2-cyclopentyl-ethyl)-6-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indole hydrochloride수율 86%

시약·촉매·용매 4

HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 21881883Oxolane--water (1/1)용매

실험 절차

1.02 g (0.0269 mol) of lithium aluminum hydride were suspended in 30 ml of THF under argon. A solution of 6.5 g (0.0207 mol) of rac-cis-3-(cyclopentyl-acetyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole in 80 ml of THF was added dropwise thereto and the mixture was boiled under reflux for 1 hour. 10 ml of THF/water 9:1, 2 ml of a 4N aqueous NaOH solution and 2 ml of water were cautiously added dropwise thereto in succession, whereupon the mixture was boiled under reflux for 15 minutes until a complete white precipitate had resulted. After filtration and concentration there was obtained an oil which was dissolved in 100 ml of ethanol. 5.1 ml (0.0245 mol) of 4.78N ethanolic HCl solution were added dropwise thereto, the mixture was stirred for 15 minutes and concentrated. The residue crystallized from 100 ml of hot ethyl acetate. There were obtained 5.87 g (86%) of rac-cis-3-(2-cyclopentyl-ethyl)-6-methoxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indole hydrochloride as white crystals with m.p. 185°-187° (dec.).

후처리

  1. temperatureunder reflux for 1 hour
  2. temperatureunder reflux for 15 minutes until a complete white precipitate
  3. customhad resulted
  4. filtrationAfter filtration
  5. concentrationconcentration there
  6. customwas obtained an oil which
  7. concentrationconcentrated
  8. customThe residue crystallized from 100 ml of hot ethyl acetate

출처 및 근거

ORD 기록
ord-1a94b311521847bb942611df34be0492
출처 데이터셋
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05318967

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