Sodium Hydroxide → rac-cis-3-(3-cyclopentyl-propyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol

HRID 1109125Notes

Reaction equation

HRID 1109125 reaction equation
[CH:1]1([CH2:6][CH2:7][CH2:8][N:9]2[C@@H:17]3[C@@H:12]([C:13]4[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C)[C:14]=4[CH2:15][CH2:16]3)[CH2:11][CH2:10]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>Br>[CH:1]1([CH2:6][CH2:7][CH2:8][N:9]2[C@@H:17]3[C@@H:12]([C:13]4[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[C:14]=4[CH2:15][CH2:16]3)[CH2:11][CH2:10]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131718463rac-cis-3-(3-cyclopentylpropyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole

Product 1

HCID 131718464rac-cis-3-(3-cyclopentyl-propyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-olYield 74%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

4.40 g (0.014 mol) of rac-cis-3-(3-cyclopentyl-propyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole were dissolved in 0.16 l of 48% aqueous HBr and boiled under reflux for 17 hours. The mixture was poured on to ~200 g of ice and treated with 180 ml of 28% aqueous NaOH solution. The mixture was extracted three times with CH2Cl2, whereupon the organic phase was washed with water, dried with MgSO4, filtered and concentrated. By chromatography of the residue over silica gel with n-hexane/ethyl acetate 1:1 there were obtained 3.1 g (74%) of rac-cis-3-(3-cyclopentyl-propyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol as an oily material.

Workup

  1. temperatureunder reflux for 17 hours
  2. extractionThe mixture was extracted three times with CH2Cl2
  3. washwhereupon the organic phase was washed with water
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b3b445fff2894ae4be1d69aa4ccfa638
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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