Chemical Properties
White powder
Uses
Methyl 1-Boc-4-piperidineacetate is used as a pharmaceutical intermediate. It can be used in the preparation of intranasal pharmaceutical compositions of CGRP inhibitors for the treatment of migraine.
Synthesis
General procedure for the synthesis of methyl N-Boc-4-piperidineacetate from tert-butyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylate: 1-tert-butoxycarbonyl-4-[(methoxycarbonyl)methylidene]piperidine (875 mg) was dissolved in ethanol (10 mL), to which 10% of palladium-carbon catalyst (~50% water content, 730 mg) was added. The reaction mixture was subjected to catalytic hydrogenation at room temperature and at atmospheric pressure for 3 days. Upon completion of the reaction, the catalyst was removed by filtration and the solvent was subsequently removed by distillation under reduced pressure to afford the target product methyl N-Boc-4-piperidineacetate (871 mg, 99% yield). The product was characterized by 1H-NMR (CDCl3): δ 1.16 (2H, m), 1.45 (9H, s), 1.65 (2H, m), 1.93 (1H, m), 2.25 (2H, d, J = 6.8 Hz), 2.72 (2H, br), 3.68 (3H, s), 4.08 (2H, br). Mass spectrometry (FAB) analysis showed m/z: 258 (M + H)+.
References
[1] Patent: EP1104754, 2001, A1
[2] Patent: EP1577302, 2005, A1. Location in patent: Page/Page column 121-122
[3] Patent: US2006/94707, 2006, A1. Location in patent: Page/Page column 43
[4] Patent: US2007/259850, 2007, A1. Location in patent: Page/Page column 79
[5] Patent: WO2011/123232, 2011, A1. Location in patent: Page/Page column 9
