HCID 90417056, compound → HCID 90417653, compound

HRID 588274Notes

Reaction equation

HRID 588274 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=3)[CH:8]=2)[NH:3]1>C1COCC1.CO.[Pd]>[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[CH:8]=2)[NH:3]1

Participants

5

Reactant 1

HCID 90417056HCID 90417056, compound

Product 1

HCID 90417653HCID 90417653, compoundYield 92.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-(2-oxoindolin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (912 mg, 2.90 mmol) in THF (10 ml) and MeOH (10 ml) was added 10% Pd/C (453 mg) and stirred at room temperature under H2 (1 atom) atmosphere for 7 h. The reaction mixture was filtered through a Celite pad and concentrated. The residue was purified by column chromatography (CHCl3/MeOH) to afford tert-butyl 4-(2-oxoindolin-5-yl)piperidine-1-carboxylate (846 mg, 92%).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-b1723cfd7b964afb8db85347d66e8756
Source dataset
uspto-grants-2016_01
Patent number
US09227962B2

Reaction notes

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