Sodium Hydroxide → HCID 131718447, compound

HRID 1109186Notes

Reaction equation

HRID 1109186 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:13][N:14]2[C@@H:22]3[C@@H:17]([C:18]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[C:19]=4[CH2:20][CH2:21]3)[CH2:16][C:15]2=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[CH:7]1([CH2:13][N:14]2[C@@H:22]3[C@@H:17]([C:18]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[C:19]=4[CH2:20][CH2:21]3)[CH2:16][CH2:15]2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 131718446HCID 131718446, compound

Product 1

HCID 131718447HCID 131718447, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

0.92 g (0.02412 mol) of lithium aluminum hydride was suspended in 40 ml of THF under argon. A solution of 3.78 g (0.01206 mol) of rac-cis-3-cyclohexylmethyl-1,3,3a,4,5,9b-hexahydro-6-methoxy-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. Then, 0.9 ml of water, 0.9 ml of 4N sodium hydroxide solution and 2.7 ml of water were cautiously added dropwise thereto in succession, whereupon the mixture was boiled at reflux until a complete white precipitate had resulted. After the addition of dry Na2SO4, filtration and concentration there was obtained an oil which was chromatographed over silica gel with cyclohexane/ethyl acetate 4:1. There were obtained 3.53 g (98%) of oily rac-cis-3-cyclohexylmethyl-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole.

Workup

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

Sources & evidence

ORD record
ord-232e5ab485e44244a20eb73deecd7b01
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

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