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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 880289Generated: October 31, 2026

Sodium Hydroxide → 3-{1-[(Tert-butoxy)carbonyl]pyrrolidin-3-yl}benzoic acid

https://huagongshe.com/reaction/880289

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium HydroxideHCID 14798—
ReactantTert-butyl 3-(3-(methoxycarbonyl)phenyl)pyrrolidine-1-carboxylateHCID 90239134—
SolventEthanolHCID 702—
SolventWaterHCID 962—
Product3-{1-[(Tert-butoxy)carbonyl]pyrrolidin-3-yl}benzoic acidHCID 5340662398%

Reaction Conditions

Temperature29 °C

Reaction Steps

To a solution of tert-butyl 3-(3-(methoxycarbonyl)phenyl)pyrrolidine-1-carboxylate (210 mg, 0.7 mmol) in EtOH (4 ml) was added a solution of NaOH (56 mg, 1.4 mmol) in H2O (1 ml) at 29° C. The mixture was stirred for 30 min at 29° C. The mixture was concentrated and the residue was treated with water and extracted with EA. The water layer was treated with 2N HCl until pH=3, extracted with EA and the combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give the title compound which was used in next step without further purification (200 mg, Yield 98.0%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08993555B2
Source datasetuspto-grants-2015_03
ORD IDord-b932856dad9c421abc16f4d6bdf5ed55
Source noteuspto-grants-2015_03