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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1253702Generated: October 30, 2026

Binap, (A+-)- → HCID 86645834, compound

https://huagongshe.com/reaction/1253702

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBinap, (A+-)-HCID 634876—
Reactant2-Bromo-5-(trifluoromethyl)pyridineHCID 2736434—
ReactantSodium t-butoxideHCID 23676156—
Reactanttert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylateHCID 34178604—
Catalystpalladium(II) acetateHCID 167845—
SolventTolueneHCID 1140—
ProductHCID 86645834HCID 8664583440%

Reaction Steps

A mixture of tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate (2.5 mmol, 1.0 eq.) and 2-bromo-5-(trifluoromethyl)pyridine (2.5 mmol, 1.0 eq.) and tBuONa (7.5 mmol, 3.0 eq.) in toluene (12 ml) was degassed with argon for 10 min. BINAP (0.15 mmol, 0.06 eq.) and Pd(OAc)2 (0.05 mmol, 0.02 eq.) were added and the reaction mixture obtained was heated under reflux for 14 h. The reaction mixture was filtered over Celite and the filtrate was concentrated in vacuo in order to obtain the crude product, which was purified by column chromatography (silica gel, 22-25% ethyl acetate in hexane), in order to obtain the desired product. Yield: 40%

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08455475B2
Source datasetuspto-grants-2013_06
ORD IDord-e07fd31bb4484ffa8d91bb9c2ac6b782
Source noteuspto-grants-2013_06