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

HRID 1944844Notes

Reaction equation

HRID 1944844 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[N:19]([CH2:22][C@@H:23]([C:32]1[CH:41]=[CH:40][C:39]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[C:38]2[C:33]=1[CH:34]=[CH:35][C:36](=[O:50])[NH:37]2)[O:24][Si](C(C)(C)C)(C)C)=[N+:20]=[N-:21]>C1COCC1>[N:19]([CH2:22][C@@H:23]([C:32]1[CH:41]=[CH:40][C:39]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[C:38]2[C:33]=1[CH:34]=[CH:35][C:36](=[O:50])[NH:37]2)[OH:24])=[N+:20]=[N-:21]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58505233(R)-5-(2-Azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one

Product 1

HCID 58505170(R)-5-(2-Azido-1-hydroxyethyl)-8-(benzyloxy)quinolin-2(1H)-oneYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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)+.

Workup

  1. concentrationthen concentrated

Sources & evidence

ORD record
ord-ec781538da52424b8bcdfcc0f66e0e31
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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