7-benzyloxy-5-{1-hydroxy-2-[2-(4-methoxy-phenyl)-1,1-dimethyl-ethylamino]-ethyl}-1H-quinolin-2-one → 7-hydroxy-5-{1-hydroxy-2-[2-(4-methoxy-phenyl)-1,1-dimethyl-ethylamino]-ethyl}-1H-quinolin-2-one

HRID 969467Notes

Reaction equation

HRID 969467 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:19])[NH:16]2)=[C:11]([CH:20]([OH:35])[CH2:21][NH:22][C:23]([CH3:34])([CH3:33])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:19])[NH:16]2)=[C:11]([CH:20]([OH:35])[CH2:21][NH:22][C:23]([CH3:33])([CH3:34])[CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[CH:10]=1

Participants

4

Reactant 1

HCID 694624247-benzyloxy-5-{1-hydroxy-2-[2-(4-methoxy-phenyl)-1,1-dimethyl-ethylamino]-ethyl}-1H-quinolin-2-one

Product 1

HCID 590172507-hydroxy-5-{1-hydroxy-2-[2-(4-methoxy-phenyl)-1,1-dimethyl-ethylamino]-ethyl}-1H-quinolin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

128 mg (0.27 mmol) 7-benzyloxy-5-{1-hydroxy-2-[2-(4-methoxy-phenyl)-1,1-dimethyl-ethylamino]-ethyl}-1H-quinolin-2-one are dissolved in 12 mL methanol and hydrogenated using palladium on charcoal as catalyst. The reaction mixture is filtered through Celite, eluted with methanol and the filtrate is freed from the solvent. Yield: 65 mg (63%); Rf=0.25 (silica gel, dichloromethane/methanol/ammonia=18:2:1).

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. washeluted with methanol

Sources & evidence

ORD record
ord-0698622a7d0f42efa825d8466ff27f24
Source dataset
uspto-grants-2007_12
Patent number
US07307076B2

Reaction notes

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