Water → 5,7-Dimethyl-8-hydroxy-9-methylamino-1,2,3,4,4a,9a-hexahydrofluorene

HRID 2051428Notes

Reaction equation

HRID 2051428 reaction equation
[CH3:1][NH2:2].[CH3:3][C:4]1[CH:16]=[C:15]([CH3:17])[C:14]([OH:18])=[C:13]2[C:5]=1[CH:6]1[CH:11]([C:12]2=O)[CH2:10][CH2:9][CH2:8][CH2:7]1.[BH4-].[Na+].O>CO.C(Cl)(Cl)Cl>[CH3:3][C:4]1[CH:16]=[C:15]([CH3:17])[C:14]([OH:18])=[C:13]2[C:5]=1[CH:6]1[CH:11]([CH:12]2[NH:2][CH3:1])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 962WaterHCID 6329Methylamine2×HCID 4311764Sodium borohydrideHCID 151571835,7-Dimethyl-8-hydroxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone

Product 1

HCID 151572475,7-Dimethyl-8-hydroxy-9-methylamino-1,2,3,4,4a,9a-hexahydrofluorene

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent5×HCID 6212ChloroformSolvent

Procedure

3.4 Milliliters of a methanol solution of 40% methylamine was added to a methanol solution containing 2 g of 5,7-dimethyl-8-hydroxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone in 20 ml of methanol and the mixture was refluxed under heating for 4 hours. Then, thereto were further added 10 ml of methanol and 3.4 ml of a methanol solution of 40% methyl amine, followed by refluxing for 6 hours. After left to stand for cooling, 3.66 g of sodium borohydride was gradually added thereto with stirring at room temperature, followed by stirring for 1 hour at the same temperature. Then, water was added to the reaction mixture and extraction was effected with chloroform. The organic layer was dried with magnesium sulfate and then the solvent was distilled off. The residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:1) and then recrystallized from ethanol to obtain 0.70 g of 5,7-dimethyl-8-hydroxy-9-methylamino-1,2,3,4,4a,9a-hexahydrofluorene.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 4 hours
  3. temperatureby refluxing for 6 hours
  4. waitAfter left
  5. temperaturefor cooling
  6. stirringby stirring for 1 hour at the same temperature
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customThe residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:1)
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d11e0f12b3dc414c8fefa5f65961fe20
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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