Sodium Hydroxide → HCID 131718471, compound

HRID 1109132Notes

Reaction equation

HRID 1109132 reaction equation
C[O:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][CH2:10][N:11]3[CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>Br>[CH2:16]([N:11]1[C@@H:12]2[C@@H:8]([C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([OH:2])[C:15]=3[CH2:14][CH2:13]2)[CH2:9][CH2:10]1)[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131718470HCID 131718470, compound

Product 1

HCID 131718471HCID 131718471, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

2.88 g (0.00936 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-phenethyl-1H-benzo[e]indole were dissolved in 0.106 l of 48% aqueous HBr and boiled under reflux for 5 hours. The mixture was poured into an ice-cold aqueous solution of 37.4 g (0.936 mol) of NaOH. Then, solid NaHO3 was added thereto and 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 cyclo-hexane/ethyl acetate 1:1 there were obtained 2.69 g (98%) of oily rac-cis-2,3,3a,4,5,9b-hexahydro-3-phenethyl-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
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1119110a237d41f1a8ba32d9fb0b6d3d
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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