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

HRID 1109196
Notes
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Reaction equation

HRID 1109196 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bdf9b97d3e4f40ee817924bcd4443fc7
Source dataset
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05318967

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes