Sodium Hydroxide → HCID 131718479, compound

HRID 1109217Notes

Reaction equation

HRID 1109217 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][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[C:13]=2[CH:12]=[CH:11][CH:10]=1.[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[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][N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 131718478HCID 131718478, compound

Product 1

HCID 131718479HCID 131718479, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

0.99 g (0.02595 mol) of lithium aluminum hydride was suspended in 50 ml of THF under argon. A solution of 4.47 g (0.01298 mol) of rac-cis-1,3,3a,4,5,9b-hexahydro-6-methoxy-3-(3-morpholin-4-yl-propyl)-2H-benzo[e]indol-2-one in 50 ml of THF was added dropwise thereto and the mixture was boiled under reflux for 2 hours. 1.0 ml of water, 1.0 ml of a 4N aqueous NaOH solution and 3.0 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 ethyl acetate/methanol 1:1. There were obtained 3.79 g (88%) of oily rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-(3-morpholin-4-yl-propyl)-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 ethyl acetate/methanol 1:1

Sources & evidence

ORD record
ord-93d39ab8a68d4c5da5aab5f3293611b0
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

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