Triethylsilane → 3-(2-Benzyloxyethyl)-2-oxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl Ester

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Reaction Steps

3-(2-Benzyloxyethyl)-2-methoxy-4-oxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound 4, 0.34 g, 0.76 mmol) was dissolved in CH2Cl2 (5 mL) in a 25-ml flask under argon. BF3OEt2 (0.18 ml, 1.52 mmol) was added dropwise to the reaction flask (fumes were released) followed by triethylsilane (0.24 g, 1.52 mmol), and the solution was stirred overnight. The CH2Cl2 was evaporated and the residue was dissolved in EtOAc and washed with saturated NaHCO3 (2×10 mL). The mixture was extracted with EtOAc (3×10 mL). The organic layer was dried over Na2SO4 and concentrated. Purification of the residue by flash column chromatography with 20% EtOAc/hexanes gave Compound 5 (0.27 g, 89%, 1:1 mixture of enantiomers) as a clear oil. Rf=0.42 (50% EtOAc/hexanes); 1H NMR (major rotamer): δ 1.62-1.72 (m, 6H), 3.25-3.50 (m, 2H), 3.68-3.90 (m, 5H), 4.49 (s, 2H), 4.75 (s, 1H), 5.14 (s, 2H), 7.26-7.34 (m, 10 H).

Provenance & Evidence