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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 916712Generated: October 26, 2026

Methyl 2-chlorobenzoate → (+)-trans-2-(2-Chloro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one

https://huagongshe.com/reaction/916712

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl 2-chlorobenzoateHCID 11895—
ReactantSodium hydrideHCID 24758—
Reactant(-)-trans-1-[2-Hydroxy-3-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4,6-dimethoxyphenyl]-1-ethanoneHCID 59318484—
SolventDimethylformamideHCID 6228—
Product(+)-trans-2-(2-Chloro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-oneHCID 59318486—

Reaction Steps

Compound(5) was converted into (−)-trans-1-[2-Hydroxy-3-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4,6-dimethoxyphenyl]-1-ethanone(compound(10) using the procedures described in examples 6 & 7. Compound(10) (0.75 g, 2.4 mmol), was reacted with methyl 2-chlorobenzoate (1.36 g, 7.9 mmol) in dry DMF (15 mL) in the presence of NaH (50%, 0.582 g, 12.9 mmol), using the procedure described in example 8 to get the title compound(11).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07271193B2
Source datasetuspto-grants-2007_09
ORD IDord-63bfd876acc647109093ef9efea21c43
Source noteuspto-grants-2007_09