ChemicalBook CAS DataBase List 1-Cbz-4-methylene-piperidine

1-Cbz-4-methylene-piperidine synthesis

4synthesis methods

Product Name:1-Cbz-4-methylene-piperidine
CAS Number:138163-12-9
Molecular formula:C14H17NO2
Molecular Weight:231.29

19099-93-5 Synthesis

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138163-12-9
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Yield: 81%

Reaction Conditions:

Stage #1:methyl-triphenylphosphonium iodide with potassium tert-butylate in tetrahydrofuran at 0; for 1 h;
Stage #2:benzyl 4-oxo-1-piperidinecarboxylate in tetrahydrofuran at 20; for 2 h;

Steps:

13-1 benzyl 4-methylenepiperidine-1-carboxylate
To a solution of iodo (methyl) triphenylphosphorane (5.20 g, 12.86 mmol) in THF (20 mL) was added potassium 2-methylpropan-2-olate (1.924 g, 17.15 mmol) at 0. After stirring for 1h at 0, benzyl 4-oxopiperidine-1-carboxylate (2 g, 8.57 mmol) was added to the mixture. And then the mixture was stirred for 2h at rt, quenched with aq NH₄Cl (10 mL) and extracted with EtOAc (3 x 20 mL) . The organic layer was dried over anhydrous Na₂SO₄, filtered and concentrated. The crude product was purified by chromatography (PE: EtOAc 40: 1) to give benzyl 4-methylenepiperidine-1-carboxylate (1.6 g, 6.92 mmol, 81 yield) . LRMS m/z (M+H) 232.1 found, 232.1 required.

References:

MERCK SHARP & DOHME CORP.;RUDD, Michael T.;MENG, Zhaoyang;WAI, Jenny;BENNETT, David Jonathan;BRNARDIC, Edward J.;LIVERTON, Nigel J.;STACHEL, Shawn J.;HAN, Yongxin;TEMPEST, Paul;ZHU, Jiuxiang;XU, Xuewang WO2018/68297, 2018, A1 Location in patent:Page/Page column 114

19099-93-5 Synthesis

19099-93-5
318 suppliers
$5.00/1g