Pyrrolidine → HCID 18407064, compound

HRID 1016503Notes

Reaction equation

HRID 1016503 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].N1CCCC1>C(O)C>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH:20]=[C:21]([C:6]2[C:5]3[C:9](=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=3)[NH:8][CH:7]=2)[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 6764936-BromoindoleHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 18407064HCID 18407064, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 6-bromoindole (390 mg, 2.0 mmol), t-butyl-4-oxo-1-piperidinecarboxylate (438 mg, 2.2 mmol), and pyrrolidine (0.42 mL, 5.0 mmol) in ethanol (10 mL) was heated at reflux for 16 hours. Solvent was evaporated and the residue subjected to chromatography on silica gel with 20% ethyl acetate/hexanes to afford a yellow solid (354 mg, 47%).

Workup

  1. temperatureat reflux for 16 hours
  2. customSolvent was evaporated

Sources & evidence

ORD record
ord-62055ef6e4a94bafa5220b3371b92ef7
Source dataset
uspto-grants-2002_11
Patent number
US06476051B2

Reaction notes

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