(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one → (R)-8-(benzyloxy)-5-(1-((tert-butyldimethylsilyl)oxy)-2-(methylamino)ethyl)quinolin-2(1H)-one

HRID 1944842Notes

Reaction equation

HRID 1944842 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:21]Br)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][NH2:32].O1CCCC1>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:21][NH:32][CH3:31])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 15606253(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-oneHCID 66615946Methylamine tetrahydrofuran

Product 1

HCID 66988338(R)-8-(benzyloxy)-5-(1-((tert-butyldimethylsilyl)oxy)-2-(methylamino)ethyl)quinolin-2(1H)-one

Procedure

A solution of (R)-8-(benzyloxy)-5-(2-bromo-1-(tert-butyldimethylsilyloxy)ethyl)quinolin-2(1H)-one (1.5 g, 3.1 mmol) in methylamine/tetrahydrofuran (2.0 M, 16 mL, 32 mmol) was heated in a sealed tube at 100° C. (oil bath) for 3 days. After allowing the mixture to cool to room temperature, it was concentrated and purified via automated flash silica gel chromatography, using a 25 g Silicycle SiliSep flash column (dichloromethane/methanol/ammonium hydroxide). Concentration of the desired fractions under reduced pressure provided the title compound. ES/MS calcd. for C25H35N2O3Si+ 439.2. Found m/z=439.3 (M+H)+.

Workup

  1. concentrationit was concentrated
  2. custompurified via automated flash silica gel chromatography

Sources & evidence

ORD record
ord-8a89852bf0d249fa82bb143079637dd4
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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