Sodium Hydroxide → HCID 131718477, compound

HRID 1109215Notes

Reaction equation

HRID 1109215 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][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].C([O-])(O)=O.[Na+]>Br>[C:19]1([CH2:18][CH2:17][CH2:16][N:11]2[C@@H:12]3[C@@H:8]([C:7]4[CH:6]=[CH:5][CH:4]=[C:3]([OH:2])[C:15]=4[CH2:14][CH2:13]3)[CH2:9][CH2:10]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 131718476HCID 131718476, compound

Product 1

HCID 131718477HCID 131718477, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

3.45 g (0.0107 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-(3-phenyl-propyl)-1H-benzo[e]indole were dissolved in 0.1211 of 48% aqueous HBr and boiled under reflux for 5 hours. The mixture was poured into an ice-cold aqueous solution of 42.8 g (1.07 mol) of NaOH. 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 over silica gel with cyclohexane/ethyl acetate 1:1 and crystallization in hexane/ethyl acetate there were obtained 2.53 g (77%) of rac-cis-2,3,3a,4,5,9b-hexahydro-3-(3-phenyl-propyl)-1H-benzo[e]indol-6-ol as whitish crystals with m.p. 98°-100°. The mother liquor was concentrated and the residue was chromatographed over silica gel with cyclohexane/ethyl acetate 1:1. There was obtained an additional 0.62 g of oily material (2.12 mmol, 19%); total yield: 96%.

Workup

  1. temperatureunder reflux for 5 hours
  2. extractionwas 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. customBy chromatography over silica gel with cyclohexane/ethyl acetate 1:1 and crystallization in hexane/ethyl acetate there

Sources & evidence

ORD record
ord-64beb5d689d442e89e79e4565737f69c
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

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