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ChemicalBook CAS DataBase List Tert-Butyl 4-((4-fluorophenyl)(hydroxy)methyl)piperidine-1-carboxylate
160296-41-3

Tert-Butyl 4-((4-fluorophenyl)(hydroxy)methyl)piperidine-1-carboxylate synthesis

8synthesis methods
137076-22-3 Synthesis
1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde

137076-22-3
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$5.00/1g

-

Yield: 82%

Reaction Conditions:

in diethyl ether at 0 - 20; for 1 h;Inert atmosphere;

Steps:

x92 x92: ferf-biitvl 4-ii4-fluorophenvl)ihydroxv)methvl)piperidine-
[0248] A solution of (4-fluorophenyl)magnesium bromide (23.44 mL, 18.76 mmol) in ether (46.9 mL) at 0°C under N2 atmosphere was treated with a solution of tert-hxityl 4- fomiylpiperidine-l-carboxylate (2 g, 9.38 mmol) in ether (4 mL) dropwise. Once the addition was complete the reaction mixture was allowed to warm up to RT and was stirred for 1 hour. The reaction mixture was quenched with saturated (aq) NH4CI and extracted with ether (1 x 150 mL) and EtOAc (1 x 2,00 mL). The organic layers were combined, dried over MgS04, filtered and the solvent removed under reduced pressure. The product was purified by column chromatography (dry packing) eluting with a gradient of 0-100% EtOAc in heptanes to give the title compound as a light yellow oil (2.37 g, 82%). ESI-MS m/z [M+H]+ 310.2.

References:

TAKEDA PHARMACEUTICAL COMPANY LIMITED;GREEN, Jason;HOPKINS, Maria;JONES, Benjamin;KIRYANOV, Andre A.;KUEHLER, Jon;MONENSCHEIN, Holger;MURPHY, Sean;NIXEY, Thomas;SUN, Huikai WO2018/183145, 2018, A1 Location in patent:Paragraph 0248