HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrabutylammonium Fluoride → (R)-5-(2-Azido-1-hydroxyethyl)-8-(benzyloxy)quinolin-2(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | (R)-5-(2-Azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one | HCID 58505233 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (R)-5-(2-Azido-1-hydroxyethyl)-8-(benzyloxy)quinolin-2(1H)-one | HCID 58505170 | 92% |
Reaction Steps
TBAF (1.0 M in THF, 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08367829B2 |
| Source dataset | uspto-grants-2013_02 |
| ORD ID | ord-8707a321e14141269585e0b7f892bfe4 |
| Source note | uspto-grants-2013_02 |