Sodium Hydroxide → HCID 131718448, compound

HRID 1109111Notes

Reaction equation

HRID 1109111 reaction equation
[CH:1]1([CH2:7][N:8]2[C@@H:16]3[C@@H:11]([C:12]4[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[C:13]=4[CH2:14][CH2:15]3)[CH2:10][CH2:9]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][N:8]2[C@@H:16]3[C@@H:11]([C:12]4[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[C:13]=4[CH2:14][CH2:15]3)[CH2:10][CH2:9]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 131718447HCID 131718447, compound

Product 1

HCID 131718448HCID 131718448, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

3.46 g (0.01155 mol) of rac-cis-3-cyclohexylmethyl-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole were dissolved in 0.13 l of 48% aqueous HBr and boiled under reflux for 5 hours. The mixture was poured into an ice-cold aqueous solution of 46.3 g (1.16 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 and then filtered, whereupon the filtrate was concentrated. By chromatography of the residue over silica gel with cyclohexane/ethyl acetate 4:1 there were obtained 3.38 g (100%) of oily rac-cis-3-cyclohexylmethyl-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 CH2Cl2
  3. washThe organic phase was washed with saturated aqueous NaHCO3 and NaCl solutions
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered, whereupon the filtrate
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-bee0e33722254f1e8f8ce8425363be6a
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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