Cesium carbonate → 2-(Methoxymethyl)-1-(3-nitrophenyl)pyrrolidine

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Benzene, 1-bromo-3-nitro-	HCID 11457	—
Reactant	2-(Methoxymethyl)pyrrolidine	HCID 143953	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Catalyst	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-(Methoxymethyl)-1-(3-nitrophenyl)pyrrolidine	HCID 68379240	72%

Reaction Steps

To a mixture of 1-bromo-3-nitrobenzene (300 mg, 1.48 mmol), 2-(methoxymethyl)pyrrolidine (187 mg, 1.63 mmol), Cs2CO3 (800 mg, 2.45 mmol), X-Phos (50 mg, 0.1 mmol), Pd(dba)2 (50 mg, 0.087 mmol) in 50 mL of dioxane were stirred at reflux overnight under N2 atmosphere. The excess of dioxane was removed under reduced pressure and the residue was purified by silica gel chromatography, eluting with a mixture of petroleum ether and ethyl acetate (5:1) to give 2-(methoxymethyl)-1-(3-nitrophenyl)pyrrolidine (250 mg, 72%) as a yellow solid. LC-MS: 237 [M+H]+, tR=1.71 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08921383B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-946ddf9cf8754a7cb133fc1d6a324bca
Source note	uspto-grants-2014_12