2-(9H-fluoren-9-yl)acetonitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6.3 mL (6.3 mmol, 2.7 eq) of a 1 M solution of LiAlH4 in THF were dissolved in 20 mL of THF in a 250 mL flask under argon. The reaction medium was cooled to −78° C. and 478 mg (2.3 mmol, 1 eq) of (9H-fluoren-9-yl)-acetonitrile in solution in 20 mL of THF were added dropwise. The temperature was allowed to rise progressively to ambient temperature. Stirring was continued for 5 hours, then the medium was hydrolysed at 0° C. by addition of 30 mL of a sodium and potassium tartrate solution. The THF was evaporated and the aqueous phase was extracted with ethyl acetate. After drying over MgSO4 and evaporation of the solvent, the crude product was subjected to chromatography over silica gel (elution gradient: CH2Cl2—CH2Cl2/MeOH: 9/1 to CH2Cl2/MeOH/NH4OH: 9/1/0.5). The 2-(9H-fluoren-9-yl)-ethylamine was obtained. to rise progressively to ambient temperature The THF was evaporated the aqueous phase was extracted with ethyl acetate After drying over MgSO4 and evaporation of the solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 610 mg (3 mmol, 1 eq) of fluoren-9-ylidene-acetonitrile in solution in 40 mL of methanol and 10 mL of ethyl acetate, then 225 mg of palladium hydroxide over coal were introduced into a 250 mL flask under a nitrogen atmosphere. The reaction medium was purged then placed under a hydrogen atmosphere (skin flask) and stirred for 6 hours while stirring. The catalyst was removed by filtration over Clarcel. The solvent was evaporated and the expected product was obtained. The reaction medium was purged while stirring The catalyst was removed by filtration over Clarcel The solvent was evaporated