Cesium carbonate → [(R)-2-(2-nitro-phenylamino)-1-phenyl-ethyl]-carbamic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	o-Iodonitrobenzene	HCID 69115	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	[(1R)-2-AMINO-1-PHENYLETHYL]-CARBAMIC ACID 1,1-DIMETHYLETHYL ESTER	HCID 15675183	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	[(R)-2-(2-nitro-phenylamino)-1-phenyl-ethyl]-carbamic acid tert-butyl ester	HCID 68777129	64.6%

Reaction Conditions

Temperature	110 °C

Reaction Steps

To a degassed solution of ((R)-2-amino-1-phenyl-ethyl)-carbamic acid tert-butyl ester (400 mg, 1.69 mmol) in toluene (10 ml), was added 2-nitroiodobenzene (423 mg, 1.69 mmol), Pd2 (dba)3 (31 mg, 0.34 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyxanthene (39 mg, 0.68 mmol) and Cs2CO3 (551 mg, 1.69 mmol). The mixture was heated at 110° C. for 24 h. It was then concentrated and the residue was purified using column chromatography (4:1, Hexanes/EtOAc) to give [(R)-2-(2-nitro-phenylamino)-1-phenyl-ethyl]-carbamic acid tert-butyl ester (390 mg, 64%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07790747B2
Source dataset	uspto-grants-2010_09
ORD ID	ord-450e4c7d594a41eb9ec256a97659774b
Source note	uspto-grants-2010_09