Phosphine, triphenyl-, hydrobromide → 3-Methylene-piperidine-1-carboxylic acid tert-butyl ester

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Reaction Steps

The title compound was prepared according to the procedure of Intermediate 71 starting from tert-butyl 3-oxopiperidine-1-carboxylate (1 g, 5.0 mmol), triphenylphosphonium bromide (2.69 g, 7.5 mmol) and n-BuLi (1.8 M; 4.2 mL, 7.5 mmol). Yield: 0.28 g (28%) after purification by flash chromatography with 10% isohexane in DCM as eluent. HPLC purity 95%, RT=2.43 min (System A; 10-97% MeCN over 3 min); 90%, RT=2.38 min (System B; 10-97% MeCN over 3 min). 1H NMR (400 MHz, CDCl3) δ ppm 1.41-1.48 (m, 9H) 1.56-1.65 (m, 2H) 2.20-2.30 (m, 2H) 3.38-3.47 (m, 2H) 3.86 (s, 2H) 4.74 (s, 1H) 4.80 (s, 1H). MS (ESI+) for C11H19NO2 m/z 142 (M-C4H8)+. *Previously reported in Tetrahedron 2002, 58, 7165-7175.

Provenance & Evidence