HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 610054
Notes
Print preview

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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 Acetate
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05998462

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes