Water → rac-cis-3-(cyclopentylacetyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole
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]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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
- customat 15°
- extractionextracted with CH2Cl2
- washThe organic phase was washed with saturated aqueous NaHCO3 and NaCl solutions
- dry with materialdried with MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ca180902a487442c8986447bf4914e65
- Source dataset
- uspto-grants-1994_06
- Patent number
- US05318966
Reaction notes
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