Sodium Hydroxide → HCID 131718467, compound

HRID 1109204Notes

Reaction equation

HRID 1109204 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][CH:18]([CH3:20])[CH3:19])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].C([O-])(O)=O.[Na+]>Br.CCCCCC>[CH3:19][CH:18]([CH3:20])[CH2:17][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

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 131718466HCID 131718466, compound

Product 1

HCID 131718467HCID 131718467, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 8058HexaneSolvent

Procedure

3.19 g (0.01167 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-(3-methyl-butyl)-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. Solid NaHCO3 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. The product obtained by chromatography of the residue over silica gel with cyclohexane/ethyl acetate 2:1 was dissolved in hot n-hexane and crystallized at room temperature. There were obtained 2.52 g (75%) of rac-cis-2,3,3a,4,5,9b-hexahydro-3-(3-methyl-butyl)-1H-benzo[e]indol-6-ol as white crystals with m.p. 70°-72° and 0.59 g (16%) of oily material from the mother liquors.

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
  7. customThe product obtained by chromatography of the residue over silica gel with cyclohexane/ethyl acetate 2:1
  8. customcrystallized at room temperature

Sources & evidence

ORD record
ord-de262ef6a64c4b1bb78dead61a4f1e2c
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

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