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	Hexane	HCID 8058	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 86731091	HCID 86731091	96%

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a suspension of Intermediate 33A (50 mg, 0.167 mmol) and Pd2(dba)3 (15.25 mg, 0.017 mmol) in toluene (2 mL) was added xantphos (28.9 mg, 0.050 mmol), benzyl piperazine-1-carboxylate (36.7 mg, 0.167 mmol), followed by sodium tert-butoxide (48.0 mg, 0.500 mmol). The reaction mixture was stirred at 70° C. for 16 h, and then filtered. The filtrate was concentrated and purified on ISCO using a 15 min gradient from 0 to 100% EtOAc in hexane to give Intermediate 33B (70 mg, 0.159 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	US08946430B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-94c8a8d39022482dbd9905e724f7c88e
Source note	uspto-grants-2015_02