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