HCID 67442235, compound → HCID 67439980, compound

HRID 1801397Notes

Reaction equation

HRID 1801397 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]([CH3:29])([O:6][C:7]1[CH:8]=[C:9]([C:13]2[C:22]([CH3:24])([CH3:23])[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:25]([O:27][CH3:28])=[O:26])[CH:19]=3)[N:14]=2)[CH:10]=[CH:11][CH:12]=1)[CH3:5]>CO.O1CCCC1.[Pd]>[CH3:1][O:2][C:3](=[O:30])[C:4]([CH3:29])([O:6][C:7]1[CH:8]=[C:9]([CH:13]2[C:22]([CH3:24])([CH3:23])[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:25]([O:27][CH3:28])=[O:26])[CH:19]=3)[NH:14]2)[CH:10]=[CH:11][CH:12]=1)[CH3:5]

Participants

5

Reactant 1

HCID 67442235HCID 67442235, compound

Product 1

HCID 67439980HCID 67439980, compoundYield 93.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(3-(1-methoxy-2-methyl-1-oxopropan-2-yloxy)phenyl)-3,3-dimethyl-3,4-dihydroquinoline-6-carboxylate (230 mg, 0.56 mmol) in methanol (5 mL) and tetrahydrofuran (5 mL) was added 10% Pd/C (100 mg). The mixture was hydrogenated by H2 balloon for 13 h. Pd/C was removed by filtration. The filtrate was concentrated to afford 216 mg of methyl 2-(3-(1-methoxy-2-methyl-1-oxopropan-2-yloxy)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as syrup. (Yield: 93%).

Workup

  1. customPd/C was removed by filtration
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-35d6689f910648ee89a9203059a37054
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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