1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 86731091, compound

Participants

Role	Name	HCID	Charge
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Benzyl piperazine-1-carboxylate	HCID 643495	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	1,1-Dimethylethyl N-[(1R)-1-(3-bromophenyl)ethyl]carbamate	HCID 67959607	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 86731091	HCID 86731091	96%

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a suspension of Intermediate 10A (50 mg, 0.17 mmol) and Pd2(dba)3 (15 mg, 0.017 mmol) in toluene (2 mL) was added Xantphos (29 mg, 0.050 mmol), benzyl piperazine-1-carboxylate (37 mg, 0.17 mmol), followed by sodium tert-butoxide (48 mg, 0.50 mmol). The reaction mixture was stirred at 70° C. for 16 h, and then filtered. The filtrate was concentrated and purified by flash chromatography using a 15 min gradient from 0 to 100% EtOAc in hexanes to give Intermediate 10B (70 mg, 0.16 mmol, 96% yield). LC-MS (ESI) m/z 440.1 (M+H), RT=2.27 min (Method B).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09394260B2
Source dataset	uspto-grants-2016_07
ORD ID	ord-58137b0e9aed42d98a9bd78becf38853
Source note	uspto-grants-2016_07