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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2167789Generated: October 31, 2026

Acetic Acid → (S)-tert-butyl 4-(3-hydroxypyrrolidin-1-yl)piperidine-1-carboxylate

https://huagongshe.com/reaction/2167789

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
Reactanttert-Butyl 4-oxopiperidine-1-carboxylateHCID 735900—
Reactant(3S)-pyrrolidin-3-olHCID 2733874—
ReactantSodium triacetoxyborohydrideHCID 5049666—
Solvent1,2-DichloroethaneHCID 11—
SolventDichloromethaneHCID 6344—
Product(S)-tert-butyl 4-(3-hydroxypyrrolidin-1-yl)piperidine-1-carboxylateHCID 8961866749.3%

Reaction Steps

Acetic acid (90 mg, 1.2 mmol) was added to solution of tert-butyl 4-oxopiperidine-1-carboxylate (300 mg, 1.5 mmol) and (S)-pyrrolidin-3-ol (140 mg, 1.7 mmol) in DCE (3 mL) at 10-15° C. and stirring was continued at the same temperature for 10 minutes. Sodium triacetoxyborohydride (957 mg, 4.5 mmol) was added portionwise to the reaction mixture and stirring was continued at 20-35° C. for 16 h. The reaction mixture was diluted with DCM, washed with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 200 mg of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09045479B2
Source datasetuspto-grants-2015_06
ORD IDord-de16a6923ff8419998f7966c7c34c8b7
Source noteuspto-grants-2015_06