Potassium Carbonate → HCID 58181382, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Benzene, 1-iodo-4-(trifluoromethyl)-	HCID 67993	—
Reactant	(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamine	HCID 11275066	—
Reactant	HCID 58181397	HCID 58181397	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	1,2-Dioxane	HCID 138570	—
Product	HCID 58181382	HCID 58181382	58.8%

Reaction Conditions

Temperature	115 °C

Reaction Steps

(R)-tert-butyl 2-hydroxy-2-((R)-3-oxomorpholin-2-yl)acetate (0.5 g, 0.002162 mol) and 4-trifluoromethylphenyl iodide (0.882 g, 1.5 eq) were dissolved in 1,2-dioxane (14 ml), to this mixture were added CuI (82 mg, 0.2 eq), K2CO3 (598 mg, 2 eq), and trans-N,N-dimethylcyclohexane-1,2-diamine (0.1 ml, 0.3 eq). The resulting solution was degassed and heated at 115° C. for 5 hours. The mixture was cooled to rt, the solid removed by filtration, solution washed with water, dried (MgSO4), and concentrated. The resulting residue was then purified by silica gel chromatography (0-20% EtOAc in hexane) to give 477 mg of compound 93-1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08987242B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-0f1255d7bcd846358eb20bbcfb79b548
Source note	uspto-grants-2015_03