8-benzyloxy-5-{1-hydroxy-2-[1-(4-trifluoromethyl-benzyl)-cyclopropylamino]-ethyl}-1H-quinolin-2-one → 8-hydroxy-5-{1-hydroxy-2-[1-(4-trifluoromethyl-benzyl)-cyclopropylamino]-ethyl}-1H-quinolin-2-one

HRID 29854Notes

Reaction equation

HRID 29854 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]([OH:37])[CH2:21][NH:22][C:23]2([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)[CH2:25][CH2:24]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]([OH:37])[CH2:21][NH:22][C:23]2([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=3)[CH2:25][CH2:24]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2

Participants

4

Reactant 1

HCID 231061178-benzyloxy-5-{1-hydroxy-2-[1-(4-trifluoromethyl-benzyl)-cyclopropylamino]-ethyl}-1H-quinolin-2-one

Product 1

HCID 231061538-hydroxy-5-{1-hydroxy-2-[1-(4-trifluoromethyl-benzyl)-cyclopropylamino]-ethyl}-1H-quinolin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

322 mg (0.63 mmol) 8-benzyloxy-5-{1-hydroxy-2-[1-(4-trifluoromethyl-benzyl)-cyclopropylamino]-ethyl}-1H-quinolin-2-one are dissolved in 10 mL methanol and hydrogenated in the presence of palladium on charcoal at 3 bar. The precipitated product is dissolved by adding methanol. The catalyst is separated off and the filtrate is evaporated down. The precipitated solid is filtered off and suspended in diethyl ether for further purification. Yield: 161 mg (61%); mass spectroscopy: [M+H]+=419.

Workup

  1. dissolutionThe precipitated product is dissolved
  2. customThe catalyst is separated off
  3. customthe filtrate is evaporated down
  4. filtrationThe precipitated solid is filtered off
  5. customsuspended in diethyl ether for further purification

Sources & evidence

ORD record
ord-994b4f23e25143e48592dc99dd94dd3f
Source dataset
uspto-grants-2008_09
Patent number
US07423035B2

Reaction notes

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