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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 12946Generated: October 26, 2026

Binap, (A+-)- → HCID 44221920, compound

https://huagongshe.com/reaction/12946

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBinap, (A+-)-HCID 634876—
ReactantSodium t-butoxideHCID 23676156—
Reactant(3aR,6aR)-Hexahydro-pyrrolo[3,4-b]pyrrole-5-carboxylic acid benzyl esterHCID 44221501—
ReactantTrifluoro-methanesulfonic acid 4'-cyano-biphenyl-4-yl esterHCID 44221918—
Catalystpalladium(II) acetateHCID 167845—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
ProductHCID 44221920HCID 44221920—

Reaction Conditions

Temperature80 °C

Reaction Steps

The product of Example 1B (trifluoro-methanesulfonic acid 4′-cyano-biphenyl-4-yl ester) (135 mg, 0.55 mmole), the product of Example 1C (198 mg, 0.61 mmole), palladium acetate (2.7 mg, 0.012 mmole), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, 20 mg, 0.033 mmole) and sodium tert-butoxide (80 mg, 0.83 mmole) were mixed in 1.5 ml of toluene and heated at 80° C. under N2 for 16 hours. The mixture was cooled to room temperature, diluted with water and extracted with dichloromethane (3×). The combined organics were dried over sodium sulfate and concentrated to provide the crude product, which was purified by chromatography (5% methanol in dichloromethane) to provide the title compound. MS: (M+H)+=424.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07728031B2
Source datasetuspto-grants-2010_06
ORD IDord-bf0d1e5abb8142eca0ac3f867410aacf
Source noteuspto-grants-2010_06