Acetone → HCID 18723451, compound

Participants

Reaction Steps

To a mixture of 0.375 g of 10% Pd/C and 6.5 g (19.4 mmol) of 1-benzyl-3-(S)-(n-propanethiocarbonyl)-4-(S)-(ethoxycarbonyl)pyrrolidine in 30 mL acetone was added dropwise 7.5 mL (47.0 mmol) of triethylsilane over 15 min. The mixture was allowed to stir for 45 min after addition was complete. The reaction mixture was filtered through a thin pad of celite and the filtrate was concentrated. The residue was purified by chromatography (silica, acetone:hexanes, 1:4) to give 4.2 g of title compound; 1H NMR (CDCl3) δ9.69 (s, 1H), 7.25-7.33 (m, 5H), 4.18 (q, 2H, J=7.1 Hz), 4.44-4.48 (m, 1H), 3.61 (d, 1H, J=13.5 Hz), 3.64 (d, 1H, J=13.5 Hz), 3.32 (m, 1H), 3.46 (m, 1H), 1.27 (t, 7.1 Hz); Mass spectrum (ESI) m/e=262 (M+1).

Provenance & Evidence