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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
ノート
印刷プレビュー

反応式

HRID 1109197 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 21881883Oxolane--water (1/1)溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-1a94b311521847bb942611df34be0492
出典データセット
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05318967

反応ノート

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