HCID 178473523, compound → HCID 178473524, compound

HRID 384487Notes

Reaction equation

HRID 384487 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][O:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([NH:27][C:28](=[O:32])[O:29][CH2:30][CH3:31])[CH2:23][CH2:22]2)[C:10]=1[CH3:33])C1C=CC=CC=1>C(O)C.C1COCC1.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH3:33][C:10]1[C:9](=[O:8])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[CH2:19][O:20][C@H:21]1[CH2:22][CH2:23][C@H:24]([NH:27][C:28](=[O:32])[O:29][CH2:30][CH3:31])[CH2:25][CH2:26]1

Participants

4

Reactant 1

HCID 178473523HCID 178473523, compound

Product 1

HCID 178473524HCID 178473524, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of ethyl (trans-4-{[4-(benzyloxy)-3-methylquinolin-2-yl]methoxy}cyclohexyl)carbamate (153 mg) in ethanol-THF (1:1, 6 mL) was added 5% Pd—BaSO4 (70 mg) under nitrogen atmosphere, followed by stirring at room temperature under hydrogen atmosphere for 1 hour. The catalyst was removed by filtration, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=95/5). The resulting solid was washed with ethyl acetate and dried to obtain ethyl {trans-4-[(3-methyl-4-oxo-1,4-dihydroquinolin-2-yl]methoxy]cyclohexyl}carbamate (88 mg) as a crystal.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=95/5)
  4. washThe resulting solid was washed with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-69d58d1073ca491ea3ef5d251d72ceda
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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