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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1020310Generated: November 2, 2026

Triethylamine → 6-Chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

https://huagongshe.com/reaction/1020310

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant1,3-Bis(diphenylphosphino)propaneHCID 81219—
ReactantN-Ethylcarbamate 5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrroleHCID 86602845—
Catalystpalladium(II) acetateHCID 167845—
SolventDimethyl SulfoxideHCID 679—
SolventMethanolHCID 887—
SolventEthyl AcetateHCID 8857—
Product6-Chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrroleHCID 1163706535%

Reaction Conditions

Temperature80 °C

Reaction Steps

To a mixture of N-ethylcarbamate-5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole, o-trifluoromethanesulfonate (60 mg, 0.14 mmol), palladium(II) acetate (6 mg, 0.028 mmol) and 1,3-bis(diphenylphosphino) propane (12 mg, 0.035 mmol) in MeOH (0.5 mL) and DMSO (0.5 mL) was added Et3N (0.2 mL, 1.4 mmol). The resulting mixture was stirred for 2 hours at 80° C. then cooled to room temperature. The reaction mixture was diluted with EtOAc (5 mL) and then washed with H2O (2 mL). The organic extract was dried over MgSO4 and concentrated to afford 15 mg (35% yield) of the subtitle compound, which was used without further purification. MS calculated for C15H18ClNO2+H: 280, observed: 280.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08716324B2
Source datasetuspto-grants-2014_05
ORD IDord-95ebd61e21da44a88cdb38237562cc6f
Source noteuspto-grants-2014_05