N-(9-Fluorenylmethoxycarbonyloxy)succinimide → HCID 54551150, compound

Participants

Reaction Conditions

Reaction Steps

The amine, (S)-2-amino-7-chloroheptanoic acid (-)-pseudoephedrinyl amide (1.8 mmol, 0.59 g) (for reference, Myers, A. G. et al. J. Am. Chem. Soc. 1995, 117, 8488), was dissolved in 7.2 mL of a heterogeneous mixture (1:1 v/v) of dioxane and saturated aqueous NaHCO3. The mixture was degassed under reduced pressure, placed under nitrogen and chilled to 0° C. To the mixture was added Fmoc-OSu (2.2 mmol, 0.73 g) in four equivalent portions over 15 min. Another 1 mL of dioxane was added to improve solubility of the Fmoc-OSu. The mixture was allowed to stir 20 min at 0° C. and 4 h at 20° C. After the mixture was concentrated under reduced pressure, it was extracted into AcOEt (250 mL). The organic layer was washed with saturated aqueous NaHCO3 (3×5 mL), saturated NaCl (3×5 mL) and dried (MgSO4). After the solvent was removed under reduced pressure, the residue obtained was purified by silica gel chromatography (AcOEt/hexanes:40/60%). The protected compound was obtained as a white foam (0.823 g, 83%) after removal of solvents under reduced pressure: [α]D25 -503.7° (c 0.01, CHCl3), Rf 0.25 (AcOEt/hexanes:1/1).

Provenance & Evidence