4-Bromo-4-[bromo(4-methoxycarbonylphenyl)methyl]piperidine-1-carboxylic tert-butyl ester → HCID 10834544, compound

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Reaction Steps

A solution of compound 4 (5.4 g 11 mmol) in methanol (300 mL) and 2.0 M NaOH (100 mL) was heated at 40° C. for 3 hrs. The solid was collected by filtration, and dried overnight under vacuum. The dry salt was dissolved in 40% acetonitrile/water, and was adjusted to pH 2 using concentrated HCl. The desired product compound 5 (3.8 g, 87%) was isolated as a white powder by filtration: 1H NMR (CDCl3) δ1.45 (s, 9H), 2.22 (dd, J=5.5 Hz, 6.1 Hz, 2H), 2.64 (dd, J=5.5 Hz, 6.1 Hz, 2H), 3.34 (dd, J=5.5 Hz, 6.1 Hz, 2H), 3.54 (dd, J=5.5 Hz, 6.1 Hz, 2H), 7.35 (d, J=6.7 Hz, 2H), 8.08 (d, J=6.7 Hz, 2H); 13 C NMR (CDCl3) δ28.3, 31.5, 34.2, 44.0, 115.3, 128.7, 129.4 130.3, 137.7, 145.2, 154.6, 170.3.

Provenance & Evidence