(+-)-3-Quinuclidinol → t-Butyl 2-(1-hydroxy-5-phenylpentyl)acrylate

Participants

Reaction Steps

t-Butyl acrylate (6.7 g, 46 mmol), 5-phenyl pentanal (3.7 g, 23 mmol) and 3-quinuclidinol (0.38 g, 3 mmol) are combined and stirred under N2. After 24 hours stirring is halted and the resulting solution is allowed to sit at ambient temperature for 16 days. TLC analysis (30% ether in petroleum ether) showed that the reaction is nearly complete. The product is purified by column chromatography (silica, 20% ether in petroleum ether) to yield t-butyl 2-(1-hydroxy-5-phenylpentyl)acrylate (6 g, 45%): 1H NMR (300 MHz, CDCl3) δ 7.29-7.24 (m, 2H), 7.18-7.14 (m, 3H), 6.10 (d, J=1.1 Hz, 1H), 5.67 (s, 1H), 4.33 (q, J=6.7 Hz, 1H), 2.74 (d, J=6.7 Hz, 1H), 2.61 (t, J=7.6 Hz, 2H), 1.70-1.53 (m, 4H), 1.50 (s, 9H), 1.50-1.32 (m, 2H); 13C NMR (75.5 MHz, CDCl3) δ 165.93, 143.91, 142.51, 128.32, 128.20, 125.57, 123.82, 81.35, 71.79, 36.17, 35.82, 31.26, 28.04, 25.54; MS (EI) m/e 291 (M+H)+.

Provenance & Evidence