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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 451817Generated: October 29, 2026

Tetrabutylammonium Fluoride → (S)-tert-butyl 1-hydroxy-3-(2-oxopiperidin-1-yl)propan-2-ylcarbamate

https://huagongshe.com/reaction/451817

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrabutylammonium FluorideHCID 2724141—
Reactant(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(2-oxopiperidin-1-yl)propan-2-ylcarbamateHCID 59201533—
SolventAcetonitrileHCID 6342—
Product(S)-tert-butyl 1-hydroxy-3-(2-oxopiperidin-1-yl)propan-2-ylcarbamateHCID 59201613100%

Reaction Conditions

Temperature55 °C

Reaction Steps

To a suspension of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-(2-oxopiperidin-1-yl)propan-2-ylcarbamate (370 mg, 0.96 mmol) in CH3CN (3 mL) was added TBAF (750 mg, 2.88 mmol). The reaction mixture was stirred for 1 h at 50-60° C. The reaction mixture was concentrated in vacuo and then EA was added. This solution was washed with brine, water and concentrated again to afford crude (S)-tert-butyl 1-hydroxy-3-(2-oxopiperidin-1-yl)propan-2-ylcarbamate (260 mg 100%), which was used in the next step without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08487108B2
Source datasetuspto-grants-2013_07
ORD IDord-dddfa08975dd4e048022240d728e4126
Source noteuspto-grants-2013_07