Ethyl Acetate → HCID 131718476, compound

HRID 1109138Notes

Reaction equation

HRID 1109138 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:21]2[CH2:20][CH2:19][C@H:18]3[C@H:14]([CH2:15][C:16](=O)[N:17]3[CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1.C(OCC)(=O)C.[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:7][O:8][C:9]1[C:21]2[CH2:20][CH2:19][C@H:18]3[C@H:14]([CH2:15][CH2:16][N:17]3[CH2:22][CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 131718475HCID 131718475, compound

Product 1

HCID 131718476HCID 131718476, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.457 g (0.01204 mol) of lithium aluminum hydride was suspended in 40 ml of THF under argon. A solution of 4.04 g (0.01204 mol) of rac-cis-1,3,3a,4,5,9b-hexahydro-6-methoxy-3-(3-phenyl-propyl)-2H-benzo[e]indol-2-one in 40 ml of THF was added dropwise thereto and the mixture was boiled under reflux for 2 hours. 10 ml of ethyl acetate and a saturated aqueous Na2SO4 solution were cautiously added dropwise thereto in succession until a complete white precipitate had resulted. After filtration and concentration there was obtained an oil which was chromatographed over silica gel with cyclohexane/ethyl acetate 3:1. There were obtained 3.46 g (89%) of oily rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-(3-phenyl-propyl)-1H-benzo[e]indole.

Workup

  1. temperatureunder reflux for 2 hours
  2. customin succession until a complete white precipitate had resulted
  3. filtrationAfter filtration
  4. concentrationconcentration there
  5. customwas obtained an oil which
  6. customwas chromatographed over silica gel with cyclohexane/ethyl acetate 3:1

Sources & evidence

ORD record
ord-c35fc236fab6463ea19b4018e4c51aac
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

Loading…