Sodium Hydroxide → HCID 131718454, compound

HRID 1109117Notes

Reaction equation

HRID 1109117 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:13][CH2:14][CH2:15][CH2:16][N:17]2[C@@H:25]3[C@@H:20]([C:21]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[C:22]=4[CH2:23][CH2:24]3)[CH2:19][C:18]2=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C1COCC1.O.[OH-].[Na+]>C1COCC1.O>[CH:7]1([CH2:13][CH2:14][CH2:15][CH2:16][N:17]2[C@@H:25]3[C@@H:20]([C:21]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[C:22]=4[CH2:23][CH2:24]3)[CH2:19][CH2:18]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)HCID 131718453HCID 131718453, compound

Product 1

HCID 131718454HCID 131718454, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.79 g (0.0208 mol) of lithium aluminum hydride was suspended in 20 ml of THF under argon. A solution of 5.60 g (0.01575 mol) of rac-cis-3-(4-cyclohexyl-butyl)-1,3,3a, 4,5,9b-hexahydro-6-methoxy-2H-benzo[e]indol-2-one in 60 ml of THF was added dropwise thereto and the mixture was boiled under reflux for 1/2 hour. 10 ml of THF/water 4:1, 4 ml of 15% aqueous NaOH solution and 2 ml of water were cautiously added dropwise thereto in succession, whereupon the mixture was boiled under reflux for 15 minutes until a complete white precipitate had resulted. After filtration, concentration and chromatography of the residue over silica gel with n-hexane/ethyl acetate 1:1 there were obtained 5.0 g (93%) of oily rac-cis-3-(4-cyclohexyl-butyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole.

Workup

  1. temperatureunder reflux for 1/2 hour
  2. temperatureunder reflux for 15 minutes until a complete white precipitate
  3. customhad resulted
  4. filtrationAfter filtration, concentration and chromatography of the residue over silica gel with n-hexane/ethyl acetate 1:1 there

Sources & evidence

ORD record
ord-a1ab5b62a5a44411a774ee26bbca9bfd
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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