1-Methyl-1,4-cyclohexadiene → (R)-5-(2-Amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-hydroxyquinolin-2(1H)-one

HRID 1472740Notes

Reaction equation

HRID 1472740 reaction equation
[N:1]([CH2:4][C@@H:5]([C:14]1[CH:23]=[CH:22][C:21]([O:24]CC2C=CC=CC=2)=[C:20]2[C:15]=1[CH:16]=[CH:17][C:18](=[O:32])[NH:19]2)[O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[N+]=[N-].CC1CC=CCC=1>[Pd].C(O)C>[NH2:1][CH2:4][C@@H:5]([C:14]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]2[C:15]=1[CH:16]=[CH:17][C:18](=[O:32])[NH:19]2)[O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

5

Reactant 2

HCID 780061-Methyl-1,4-cyclohexadieneHCID 58505233(R)-5-(2-Azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one

Product 1

HCID 59023604(R)-5-(2-Amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-hydroxyquinolin-2(1H)-oneYield 90.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To an ice-cooled suspension of palladium on activated carbon (4.50 g, 10% w/w) and (R)-5-(2-azido-1-(tert-butyldimethylsilyloxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one (4.50 g, 10.0 mmol) in ethanol (50 mL) was added drop-wise 1-methyl-1,4-cyclohexadiene (11.0 mL, 97.9 mmol). The coolant was removed, and the suspension stirred at ambient temperature for 10 minutes and then heated to 50° C. for one hour. The reaction mixture was allowed to cool and the suspension filtered through celite. The filter-cake was washed with further ethanol, and the combined filtrates concentrated under reduced pressure. The residue was triturated with acetonitrile to afford the title compound (3.03 g, 90%).

Workup

  1. customThe coolant was removed
  2. temperatureheated to 50° C. for one hour
  3. temperatureto cool
  4. filtrationthe suspension filtered through celite
  5. washThe filter-cake was washed with further ethanol
  6. concentrationthe combined filtrates concentrated under reduced pressure
  7. customThe residue was triturated with acetonitrile

Sources & evidence

ORD record
ord-d1e34c17b5b44139a681572c165e432a
Source dataset
uspto-grants-2015_04
Patent number
US09012644B2

Reaction notes

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