Water → (4-Fluoro-phenyl)-(4-methyl-piperidin-4-yl)-methanone

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Pivalic anhydride	HCID 15234	—
Reactant	4-Fluorophenylboronic acid	HCID 285645	—
Reactant	1-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acid	HCID 23282848	—
Catalyst	palladium(II) acetate	HCID 167845	—
Catalyst	Ferrocene-1,1'-bis-(diphenylphosphine)	HCID 635956	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(4-Fluoro-phenyl)-(4-methyl-piperidin-4-yl)-methanone	HCID 20530715	5%

Reaction Conditions

Temperature	60 °C

Reaction Steps

N-boc-4-methyl-4-piperidinecarboxylic acid (4 g, 16 mol), 4-Fluorobenzeneboronic acid (2.7 g, 20 mol), Pivalic anhydride (4.6 g, 25 mmol), Pd(OAc)2 (0.111 g, 0.4 mol), 1,1′-Bis(diphenylphosphino)ferrocene (0.319 g, 0.1 mol) and (0.7 mL, 41 mmol) of water were mixed together in 20 mL of tetrahydrofuran and the mixture heated at 60° C. overnight. The reaction mixture was filtrated and the solvent was removed under vacuum. The residue was purified with column chromatography on silica using n-heptane-EtOAc (4:1) to yield 0.216 g (5%) of the title compound. MS (m/e): 322.0 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08039490B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-2f7587508095417aad44c18bd6845af8
Source note	uspto-grants-2011_10