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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 458886Generated: October 27, 2026

Tetrahydrofuran → (3R)-3-{[(9-hydroxy-9H-fluoren-9-yl)carbonyl]oxy}-1-methyl-1-(4-oxo-4-phenylbutyl)pyrrolidinium formate

https://huagongshe.com/reaction/458886

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
Reactant4-ChlorobutyrophenoneHCID 253533—
Reactant9-Hydroxy-9H-fluorene-9-carboxylic acid (3R)-1-methylpyrrolidin-3-yl esterHCID 86602259—
Product(3R)-3-{[(9-hydroxy-9H-fluoren-9-yl)carbonyl]oxy}-1-methyl-1-(4-oxo-4-phenylbutyl)pyrrolidinium formateHCID 694802337%

Reaction Steps

0.575 g (1.858 mmol) of 9-Hydroxy-9H-fluorene-9-carboxylic acid (3R)-1-methylpyrrolidin-3-yl ester (Intermediate I-10) and 1.018 g (5.576 mmol) of 4-chloro-1-phenylbutan-1-one in 6 ml of THF were refluxed for 20 days. After this time THF was poured off, and the residue was washed with THF in order to eliminate the alkylating agent. The product obtained (234 mg) was purified by preparative HPLC-MS to give 65 mg (7%) of the title compound (mixture of two stereoisomers) as a formate.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07192978B2
Source datasetuspto-grants-2007_03
ORD IDord-242c962815b6439d85c4a09cc5133184
Source noteuspto-grants-2007_03