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

HRID 1944843Notes

Reaction equation

HRID 1944843 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH2:21][NH:22][CH3:23])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1>CO.[Pd]>[Si:25]([O:24][C@H:20]([C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:19])[NH:17]2)[CH2:21][NH:22][CH3:23])([C:28]([CH3:30])([CH3:31])[CH3:29])([CH3:27])[CH3:26]

Participants

4

Reactant 1

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

Product 1

HCID 66988438(R)-5-(1-((tert-butyldimethylsilyl)oxy)-2-(methylamino)ethyl)-8-hydroxyquinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Intermediate 3 was dissolved in MeOH (25 mL) and Pd/C (10% w/w, 100 mg) was added. The resulting suspension was attached to a balloon filled with H2 and stirred for 7 hours. The reaction mixture was filtered through Celite diatomaceous earth and concentrated to give provide the title compound as a hard foam. ES/MS calcd. for C18H29N2O3Si+ 349.2. Found m/z=349.2 (M+H)+.

Workup

  1. additionfilled with H2
  2. filtrationThe reaction mixture was filtered through Celite diatomaceous earth
  3. concentrationconcentrated
  4. customto give

Sources & evidence

ORD record
ord-4c43d8c812d84d1b93a0ff1db2d457fb
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

Loading…