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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2074240Generated: November 1, 2026

Methanol → 3-{2-[1-(Tert-butoxycarbonyl)-4-piperidinyl]ethyl]benzoic acid

https://huagongshe.com/reaction/2074240

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantTetrahydrofuranHCID 8028—
ReactantSodium HydroxideHCID 14798—
ReactantTert-butyl 4-{2-[3-(methoxycarbonyl)phenyl]ethyl}-1-piperidinecarboxylateHCID 57507758—
SolventEthyl AcetateHCID 8857—
Product3-{2-[1-(Tert-butoxycarbonyl)-4-piperidinyl]ethyl]benzoic acidHCID 5742182699.8%

Reaction Conditions

Temperature60 °C

Reaction Steps

Aqueous 1 M sodium hydroxide solution (196 ml) was added to a THF (200 ml)/methanol (50 ml) mixed solution of tert-butyl 4-{2-[3-(methoxycarbonyl)phenyl]ethyl}-1-piperidinecarboxylate (45.4 g), followed by stirring at 60° C. for 2 hours. The organic solvent was evaporated under reduced pressure, and under ice cooling, 0.5 M hydrochloric acid (400 ml) was added to the residue. The reaction liquid was diluted with EtOAc, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 3-{2-[1-(tert-butoxycarbonyl)-4-piperidinyl]ethyl}benzoic acid (43.5 g) was obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07919494B2
Source datasetuspto-grants-2011_04
ORD IDord-7fd5764bb5d74b3687e60ca3d54310ad
Source noteuspto-grants-2011_04