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

HRID 1109170Notes

Reaction equation

HRID 1109170 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)[NH:17]3)[C:13]=2[CH:12]=[CH:11][CH:10]=1.O.[OH-].[Na+]>O1CCCC1>[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][NH:17]3)[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 131718423rac-cis-1,3,3a,4,5,9b-hexahydro-6-methoxy-2H-benzo[e]indol-2-one

Product 1

HCID 101650127rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indoleYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 25 g (0.66 mol) of lithium aluminum hydride in 2 l of tetrahydrofuran was treated portionwise with 71.5 g (0.33 mol) of rac-cis-1,3,3a,4,5,9b-hexahydro-6-methoxy-2H-benzo[e]indol-2-one. The mixture was boiled at reflux overnight, cooled to about -10° and then hydrolyzed by the successive dropwise addition of 25 ml of water, 25 ml of 15 percent sodium hydroxide solution and 75 ml of water. The solid residue was filtered off and rinsed with methylene chloride. The organic phases were concentrated. The residue was dissolved in methylene chloride and the solution was dried with sodium sulphate. After distillation of the solvent in a vacuum and crystallization in a refrigerator there were obtained 64.0 g (96%) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole as grey crystals.

Workup

  1. temperatureat reflux overnight
  2. temperaturecooled to about -10°
  3. filtrationThe solid residue was filtered off
  4. washrinsed with methylene chloride
  5. concentrationThe organic phases were concentrated
  6. dissolutionThe residue was dissolved in methylene chloride
  7. dry with materialthe solution was dried with sodium sulphate
  8. distillationAfter distillation of the solvent
  9. customin a vacuum and crystallization in a refrigerator

Sources & evidence

ORD record
ord-04ba0b827a324e06bd52477f19356ef9
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

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