Water → N-(2,7-di-tert-butyl-9-fluorenylmethyl)piperidine

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Reaction Steps

Piperidine Cleavage of 2,7-Di-tert-butyl-9-trimethylsilyl-9-fluorenylmethyl Carbanilate: A solution of 0.4 g of DT-Fmoc-analine in 8.0 mL of piperidine was stirred at room temperature for 22 hours. The mixture was poured into 50 mL of cold water and stirred for 10 minutes. The precipitate was removed by filtration, rinsed with water (2×5 mL), and dried in air to afford 0.30 g (100%) of crude N-(2,7-di-tert-butyl-9-fluorenylmethyl)piperidine as an off-white solid. Recrystallization from CH3OH--CHCl3 (2:1) gave 0.248 g (82.53%) of the pure amine as white crystals, m.p. 159°-160° C., identified by mixture melting point, and IR and NMR spectral comparison with a sample obtained by piperidine cleavage of DT-Fmoc-PCA.

Provenance & Evidence