Potassium Carbonate → 5-(2-Oxo-pyrrolidin-1-yl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Pyrrolidone	HCID 12025	—
Reactant	1,2-Diaminocyclohexane, trans-	HCID 43806	—
Reactant	tert-Butyl 5-iodoisoindoline-2-carboxylate	HCID 57753580	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	5-(2-Oxo-pyrrolidin-1-yl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester	HCID 57753514	—

Reaction Conditions

Temperature	140 °C

Reaction Steps

Lit. J. Am. Chem. Soc. 2001, 123, 7727-7729. To a stirred suspension of 0.58 mmol 5-iodo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (Example A38(b)) in 4 ml dioxane were added 0.12 mmol copper(I) iodide, 1.74 mmol potassium carbonate, 0.17 mmol trans-1,2-diaminocyclohexane and 2.90 mmol 2-pyrrolidone and the reaction mixture was stirred at 140° C. for 16 h. The mixture was then cooled to room temperature, filtered, and the filtrate was concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a white solid. MS (m/e): 247.3 ([M+H−Me2C═CH2]+, 100%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07557114B2
Source dataset	uspto-grants-2009_07
ORD ID	ord-df9a2c351edd4098ba0aa558fc97d44a
Source note	uspto-grants-2009_07