Sodium Hydroxide → HCID 131718455, compound

HRID 1109118Notes

Reaction equation

HRID 1109118 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][N:11]2[C@@H:19]3[C@@H:14]([C:15]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C)[C:16]=4[CH2:17][CH2:18]3)[CH2:13][CH2:12]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>Br>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][N:11]2[C@@H:19]3[C@@H:14]([C:15]4[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[C:16]=4[CH2:17][CH2:18]3)[CH2:13][CH2:12]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131718454HCID 131718454, compound

Product 1

HCID 131718455HCID 131718455, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

5.0 g (0.0146 mol) of rac-cis-3-(4-cyclohexyl-butyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole were dissolved in 0.17 l of 48% aqueous HBr and boiled under reflux for 5 hours. The mixture was poured on to ~200 g of ice and treated with 200 ml of 28% aqueous NaOH solution. The mixture was extracted three times with ethyl acetate, whereupon the organic phase was washed with saturated sodium chloride solution, dried with MgSO4, filtered and concentrated. By chromatography of the residue over silica gel with n-hexane/ethyl acetate 1:1 there were obtained 4.3 g (90%) of oily rac-cis-3-(4-cyclohexyl-butyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol.

Workup

  1. temperatureunder reflux for 5 hours
  2. extractionThe mixture was extracted three times with ethyl acetate
  3. washwhereupon the organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9fbce0d258c8457796450a8ad61eb6b2
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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