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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 874072Generated: October 29, 2026

Potassium Carbonate → (S)-tert-butyl 2-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yloxy)ethylcarbamate

https://huagongshe.com/reaction/874072

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
Reactanttert-Butyl N-(2-bromoethyl)carbamateHCID 4103526—
Reactant(S)-5-(1-Methylpyrrolidin-2-yl)pyridin-3-olHCID 58537397—
SolventDimethylformamideHCID 6228—
Product(S)-tert-butyl 2-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yloxy)ethylcarbamateHCID 5853743134.3%

Reaction Steps

(S)-5-(1-Methylpyrrolidin-2-yl)pyridin-3-ol (preparation 10) (175 mg, 0.98 mmol), tert-butyl 2-bromoethylcarbamate (550 mg, 2.45 mmol) and potassium carbonate (676 mg, 4.9 mmol) in DMF (7 mL) were heated at 90° C. for 16 hours. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate, dried over MgSO4 and evaporated. The crude product was purified by flash chromatography (5%→10% MeOH in DCM) to give the title compound as a yellow oil (108 mg, 34%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08980276B2
Source datasetuspto-grants-2015_03
ORD IDord-f9183f1101484b18b550a9c7b67434f9
Source noteuspto-grants-2015_03