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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1612468Generated: October 30, 2026

Citric Acid → t-Butyl 2-methoxy-6-(2-oxopyrrolidin-1-yl)pyridine-4-carboxylate

https://huagongshe.com/reaction/1612468

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCitric AcidHCID 311—
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
Reactantt-Butyl 2-(4-bromobutyramido)-6-methoxypyridine-4-carboxylateHCID 22253030—
Solvent1,4-DioxaneHCID 31275—
Productt-Butyl 2-methoxy-6-(2-oxopyrrolidin-1-yl)pyridine-4-carboxylateHCID 2225298374.7%

Reaction Steps

t-Butyl 2-(4-bromobutyramido)-6-methoxypyridine-4-carboxylate (D56) (0.47 g) was dissolved in dioxan and treated with DBU (0.31 mL; 1 eq.). After stirring for 0.5 h, further DBU (0.31 mL; 1 eq.) was added. Stirring was continued for 2 h and the mixture was poured into citric acid solution (10% aq.) and extracted twice with ethyl acetate. The combined extracts were washed with aq. bicarbonate, water and brine, dried (MgSO4) and evaporated, giving the title compound (D57) as a beige solid (0.275 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06992103B2
Source datasetuspto-grants-2006_01
ORD IDord-c5770a83eb4146ecabe8c1a63dddbe2a
Source noteuspto-grants-2006_01