Ethyl Acetate → HCID 131718470, compound

HRID 1109207Notes

Reaction equation

HRID 1109207 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][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 131718469HCID 131718469, compound

Product 1

HCID 131718470HCID 131718470, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.3557 g (0.00936 mol) of lithium aluminum hydride was suspended in 40 ml of THF under argon. A solution of 3.01 g (0.00936 mol) of rac-cis-1,3,3a,4,5,9b-hexahydro-6-methoxy-3-phenethyl-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 were obtained 2.9 g (100%) of oily rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-phenethyl-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

Sources & evidence

ORD record
ord-2442051fddf945c7a1f84ade18628ec2
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

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