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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1693243Generated: October 30, 2026

Benzophenone imine → HCID 57827439, compound

https://huagongshe.com/reaction/1693243

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzophenone imineHCID 136809—
ReactantBinap, (A+-)-HCID 634876—
ReactantSodium t-butoxideHCID 23676156—
ReactantHCID 57827764HCID 57827764—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
ProductHCID 57827439HCID 57827439—

Reaction Conditions

Temperature85 °C

Reaction Steps

Benzophenone imine (244 μL), BINAP (60.6 mg), tris(dibenzylideneacetone)dipalladium (0) (44.6 mg) and sodium tert-butoxide (233 mg) were added to a solution of (±)-N,N-bis(tert-butoxycarbonyl)[(3aS*,7aR*)-7a-(3-bromophenyl)-3a,6,7,7a-tetrahydro-4H-pyrano[4,3-d]thiazol-2-yl]amine (250 mg) in toluene (20 mL). After replacement with nitrogen, the mixture was stirred at 85° C. for four hours. The reaction solution was returned to room temperature, and water was added to the reaction mixture. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (165 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08158620B2
Source datasetuspto-grants-2012_04
ORD IDord-ae4b2ed6eaac470182ace674fd4ea8af
Source noteuspto-grants-2012_04