Sodium Hydroxide → HCID 131718452, compound

HRID 1109191Notes

Reaction equation

HRID 1109191 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][N:10]2[C@@H:18]3[C@@H:13]([C:14]4[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[C:15]=4[CH2:16][CH2:17]3)[CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].C([O-])(O)=O.[Na+]>Br>[CH:1]1([CH2:7][CH2:8][CH2:9][N:10]2[C@@H:18]3[C@@H:13]([C:14]4[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[C:15]=4[CH2:16][CH2:17]3)[CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 131718451HCID 131718451, compound

Product 1

HCID 131718452HCID 131718452, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

2.62 g (0.008 mol) of rac-cis-3-(3-cyclohexyl-propyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole were dissolved in 0.09 of 48% aqueous HBr and boiled under the reflux for 5 hours. The mixture was poured into an ice-cold aqueous solution of 32 g (0.8 mol) of NaOH, whereupon, after the addition of solid NaHCO3, the mixture was extracted three times with CH2Cl2. The organic phase was washed with saturated aqueous NaHCO3 and NaCl solutions, dried with Na2SO4, filtered and concentrated. By chromatography of the residue over silica gel with cyclohexane/ethyl acetate 1:1 there was obtained 0.92 g (37%) of oily rac-cis-3-(3-cyclohexyl-propyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol.

Workup

  1. temperaturereflux for 5 hours
  2. extractionthe mixture was extracted three times with CH2Cl2
  3. washThe organic phase was washed with saturated aqueous NaHCO3 and NaCl solutions
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-94e53cfd41bb453ea1f98172d024a7ce
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

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