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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 605792Generated: October 31, 2026

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

https://huagongshe.com/reaction/605792

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 numberUS07915261B2
Source datasetuspto-grants-2011_03
ORD IDord-064a3b90e1c54d108cd73c4071052f12
Source noteuspto-grants-2011_03