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

HRID 1109120노트

반응식

HRID 1109120 반응식
[CH3:1][O:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][CH2:10][NH:11]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH2:23]1[CH2:27][CH2:26][CH:25]([CH2:28][C:29](Cl)=[O:30])[CH2:24]1.O>C(Cl)Cl>[CH:25]1([CH2:28][C:29]([N:11]2[C@@H:12]3[C@@H:8]([C:7]4[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:15]=4[CH2:14][CH2:13]3)[CH2:9][CH2:10]2)=[O:30])[CH2:26][CH2:27][CH2:23][CH2:24]1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 3485182Cyclopentylacetyl chlorideHCID 101650127rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole

생성물 1

HCID 131718458rac-cis-3-(cyclopentylacetyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole수율 84.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

5.0 g (0.0246 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole were dissolved in 100 ml of CH2Cl2, 4.1 ml (0.0295 mol) of triethylamine were added thereto and a solution of 4.3 ml (0.0295 mol) of 3-cyclopentylacetyl chloride in 40 ml of CH2Cl2 was added dropwise thereto at 15° under argon. The mixture was stirred at room temperature for 1/2 hour, then poured into water and extracted with CH2Cl2. The organic phase was washed with saturated aqueous NaHCO3 and NaCl solutions, dried with MgSO4, filtered and concentrated. By chromatography of the residue over silica gel with n-hexane/ethyl acetate 3:1 there were obtained 6.50 g (84%) of pale yellow oily rac-cis-3-(cyclopentylacetyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole.

후처리

  1. customat 15°
  2. extractionextracted with CH2Cl2
  3. washThe organic phase was washed with saturated aqueous NaHCO3 and NaCl solutions
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ca180902a487442c8986447bf4914e65
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05318966

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