Sodium Hydroxide → HCID 131718455, compound

HRID 1109194Notes

Reaction equation

HRID 1109194 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 0.171 of 48% aqueous HBr and boiled under reflux for 5 hours. The mixture was poured onto ~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-cec9afe3aa484bee93c29a26a9979326
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

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