Sodium Hydroxide → rac-cis-3-(3-cyclopentylpropyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole

HRID 1109124Notes

Reaction equation

HRID 1109124 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:12][CH2:13][C:14]([N:16]2[C@@H:24]3[C@@H:19]([C:20]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[C:21]=4[CH2:22][CH2:23]3)[CH2:18][CH2:17]2)=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.C1COCC1.O.[OH-].[Na+]>C1COCC1.O>[CH:7]1([CH2:12][CH2:13][CH2:14][N:16]2[C@@H:24]3[C@@H:19]([C:20]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[C:21]=4[CH2:22][CH2:23]3)[CH2:18][CH2:17]2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)HCID 131718462rac-cis-3-(3-cyclopentyl-propionyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole

Product 1

HCID 131718463rac-cis-3-(3-cyclopentylpropyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indoleYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.71 g (0.0187 mol) of lithium aluminum hydride was suspended in 20 ml of THF under argon. A solution of 4.7 g (0.01435 mol) of rac-cis-3-(3-cyclopentyl-propionyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole in 50 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 a 15% aqueous NaOH solution and 2 ml of water were cautiously added dropwise thereto in succession, whereupon the mixture was boiled under reflux for 10 minutes until a complete white precipitate had resulted. After filtration and concentration there was obtained an oil which was chromatographed over silica gel with n-hexane/ethyl acetate 1:1. There were obtained 4.40 g (98%) of rac-cis-3-(3-cyclopentyl-propyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole as a yellowish, oily material.

Workup

  1. temperatureunder reflux for 1/2 hour
  2. temperatureunder reflux for 10 minutes until a complete white precipitate
  3. customhad resulted
  4. filtrationAfter filtration
  5. concentrationconcentration there
  6. customwas obtained an oil which
  7. customwas chromatographed over silica gel with n-hexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-c82e6cc77f904a2f9dc93ed733e00ced
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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