Chlorotrimethylsilane → Methyl 4-phenylpiperidine-4-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Chlorotrimethylsilane	HCID 6397	—
Reactant	4-Piperidinecarboxylic acid, 4-phenyl-, 4-methylbenzenesulfonate (1:1)	HCID 2723657	—
Solvent	Methanol	HCID 887	—
Product	Methyl 4-phenylpiperidine-4-carboxylate	HCID 545827	—

Reaction Conditions

Temperature	50 °C

Reaction Steps

To a solution of 4-phenyl-piperidine-4-carboxylic acid tosylate (4.6 g, 20 mmol) in MeOH (25 mL) is added TMSCl (10 mL) and the reaction mixture is stirred at 50° C. for 15 h. The reaction mixture is cooled and evaporated. The residue is taken up in MeOH (5 mL), poured into sat. Na2CO3 (100 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic extracts are dried (Na2SO4), filtered and evaporated to provide the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07375227B2
Source dataset	uspto-grants-2008_05
ORD ID	ord-0aec7df2661a44adb273920fed2607e2
Source note	uspto-grants-2008_05