ChemicalBook CAS DataBase List tert-butyl 4-(4-(methoxycarbonyl)benzyl)piperidine-1-carboxylate

tert-butyl 4-(4-(methoxycarbonyl)benzyl)piperidine-1-carboxylate synthesis

6synthesis methods

Product Name:tert-butyl 4-(4-(methoxycarbonyl)benzyl)piperidine-1-carboxylate
CAS Number:210964-04-8
Molecular formula:C19H27NO4
Molecular Weight:333.42

4-(4-methoxycarbonylbenzylidene)piperidine-1-carboxylic acid tert-butyl ester

209808-15-1
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tert-butyl 4-(4-(methoxycarbonyl)benzyl)piperidine-1-carboxylate

210964-04-8
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Yield:210964-04-8 100%

Reaction Conditions:

palladium monocarbide in methanol;

Steps:

R.123.1 tert-Butyl 4-(4-Methoxycarbonylbenzyl)piperidine-1-carboxylate

A mixture of tert-butyl 4-(4-methoxycarbonylbenzylidene)piperidine-1-carboxylate (6 g, 18 mmol) in methanol (150 ml) was hydrogenated over 10% palladium carbon (50% wet, 1 g) for 5 h at room temperature. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel 90 g, ethyl acetate/hexane=1/10) to obtain the title compound (6.1 g, 100%) as pale yellow oil. ¹H NMR (CDCl₃) δ 1.05-1.42 (2H, m), 1.45 (9H, s), 1.55-1.77 (3H, m), 2.59 (2H, d, J=7.0 Hz), 2.57-2.69 (2H, m), 3.91 (3H, s), 4.04-4.18 (2H, m), 7.21 (2H, d, J=8.0 Hz), 7.96 (2H, d, J=8.0 Hz).

References:

US6562978,2003,B1

619-42-1 Synthesis