1,4-Bis(diphenylphosphino)butane → HCID 86598905, compound

Participants

Role	Name	HCID	Charge
Reactant	1,4-Bis(diphenylphosphino)butane	HCID 82124	—
Reactant	Allylethyl carbonate	HCID 137020	—
Reactant	tert-Butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate	HCID 86598896	—
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	Tetrahydrofuran	HCID 8028	—
Product	HCID 86598905	HCID 86598905	715.2%

Reaction Conditions

Temperature	65 °C

Reaction Steps

To a solution of tert-butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate obtained in Example 5-7 (510 mg) in tetrahydrofuran (5.0 mL), were added 1,4-bis(diphenylphosphino)butane (64.8 mg), tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (39.3 mg) and allyl ethyl carbonate (0.4 mL). The mixture was stirred at 65° C. for 4 hrs. The resulting mixture was evaporated in vacuo and the residue was chromatographed on silica gel eluting with ethyl acetate to give the target compound (408 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07186731B2
Source dataset	uspto-grants-2007_03
ORD ID	ord-979686a2bd8849ac9d0f8a5ad53e7b93
Source note	uspto-grants-2007_03