Benzophenone imine → HCID 76831142, compound

Participants

Role	Name	HCID	Charge
Reactant	Benzophenone imine	HCID 136809	—
Reactant	Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane	HCID 11618717	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	HCID 76831082	HCID 76831082	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Solvent	Water	HCID 962	—
Solvent	Toluene	HCID 1140	—
Product	HCID 76831142	HCID 76831142	85.2%

Reaction Conditions

Temperature	105 °C

Reaction Steps

Under argon in a sealed tube was added to a solution of (1SR,7RS)-1-(5-bromo-2-fluoro-phenyl)-5-oxa-2-aza-bicyclo[5.1.0]octan-3-one (intermediate B10A) (405 mg, 1.349 mmol) in toluene (9 ml), sodium tert-butoxide (NaOBut) (389 mg, 4.05 mmol), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (t-Bu X-phos) (57 mg, 10 mol %) and tris(dibenzylideneacetone)dipalladium chloroform complex (Pd2(dba)3.CHCl3)(42 mg, 3 mol %) followed by benzophenone imine (453 uL, 2.7 mmol). The tube was sealed under argon and the mixture was stirred at 105° C. for 18 h to 2.5 days. The mixture was cooled to 23° C., poured into water, extracted with ethyl acetate, and the organic layer was washed with brine and dried over sodium sulfate. Removal of the solvent in vacuum left a brown oil, which was purified by silica gel column chromatography with n-heptane/ethyl acetate to give the title compound as a yellow foam (460 mg, 85%). MS (ISP): m/z=401.3 [(M+H)+].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08673894B2
Source dataset	uspto-grants-2014_03
ORD ID	ord-5dc78d6f7ac3408b97893e0e058f76ae
Source note	uspto-grants-2014_03