Ethanol → (R)-5-Methyl-3-[(pyrrolidin-2-yl)carbonyl]-1H-indole

HRID 610054

Reaction equation

HRID 610054 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH3:11][CH2:12][OH:13]>CCOC(C)=O.[Pd]>[NH3:7].[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:12]([C@H:11]1[CH2:4][CH2:5][CH2:6][NH:7]1)=[O:13]

Participants

6

Reactant 2

HCID 702EthanolHCID 119785-Methylindole

Product 2

HCID 222AmmoniaHCID 54138762(R)-5-Methyl-3-[(pyrrolidin-2-yl)carbonyl]-1H-indoleYield 15%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (R)-3-[(N-benzyloxycarbonylpyrrolidin-2-yl)carbonyl)]-5-methyl-1H-indole (Example 5b) in EtOAc (10 mL) was added EtOH (10 mL) and Pd/C (1.3 g). The reaction mixture was stirred at room temperature under a hydrogen atmosphere until the starting material was consumed. At this time, the reaction mixture was filtered through celite and the solvent was evaporated. The crude product was purified by column chromatography (4:1 CHCl3 : NH3 (2M in MeOH) to yield the title compound (121.5 mg, 15%) as a white solid (mp 194-196° C.).

Workup

  1. customwas consumed
  2. filtrationAt this time, the reaction mixture was filtered through celite
  3. customthe solvent was evaporated
  4. customThe crude product was purified by column chromatography (4:1 CHCl3

Sources & evidence

ORD record
ord-d62deb98251646318f3c6835cfcebfff
Source dataset
uspto-grants-1999_12
Patent number
US05998462

Linked notes

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