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

HRID 1109123Notes

Reaction equation

HRID 1109123 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.[CH:23]1([CH2:28][CH2:29][C:30](Cl)=[O:31])[CH2:27][CH2:26][CH2:25][CH2:24]1.O>C(Cl)Cl>[CH:23]1([CH2:28][CH2:29][C:30]([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:31])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 660393-Cyclopentylpropionyl chlorideHCID 101650127rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole

Product 1

HCID 131718462rac-cis-3-(3-cyclopentyl-propionyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indoleYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.06 g (0.020 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole were dissolved in 80 ml of CH2Cl2, 3.35 ml (0.024 mol) of triethylamine were added thereto and a solution of 3.7 ml (0.024 mol) of 3-cyclopentylpropionyl chloride in 40 ml of CH2Cl2 was added dropwise thereto at 20° under argon. The mixture was stirred at room temperature for 1 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 1:1 there were obtained 4.75 g (72.5%) of rac-cis-3-(3-cyclopentyl-propionyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole as a pale yellow, oily material.

Workup

  1. customat 20°
  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-caf3cf74fcd44fbe87cfacb9702d4869
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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