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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1944844Generated: October 30, 2026

Tetrabutylammonium Fluoride → (R)-5-(2-Azido-1-hydroxyethyl)-8-(benzyloxy)quinolin-2(1H)-one

https://huagongshe.com/reaction/1944844

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrabutylammonium FluorideHCID 2724141—
Reactant(R)-5-(2-Azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-oneHCID 58505233—
SolventTetrahydrofuranHCID 8028—
Product(R)-5-(2-Azido-1-hydroxyethyl)-8-(benzyloxy)quinolin-2(1H)-oneHCID 5850517092%

Reaction Steps

A 1.0 M (THF) solution of TBAF (0.443 mL, 0.443 mmol) was added to a stirring solution of Intermediate 1 (200 mg, 0.443 mmol) in THF (4 mL) at rt. The resulting mixture was stirred over night then concentrated. Chromatography (1:3, Hexanes/EtOAc) afforded the title compound (137 mg, 92%) as an off-white solid. ES/MS calcd. for C18H17N4O3+ 337.1. Found m/z=337.2 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08394829B2
Source datasetuspto-grants-2013_03
ORD IDord-ec781538da52424b8bcdfcc0f66e0e31
Source noteuspto-grants-2013_03