Pyrrolidine → HCID 18407066, compound

HRID 1016499Notes

Reaction equation

HRID 1016499 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[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:4]2[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[F:1])[NH:6][CH:5]=2)[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 27745024-Fluoroindole

Product 1

HCID 18407066HCID 18407066, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 4-fluoroindole (400 mg, 3.0 mmol), t-butyl-4-oxo-1-piperidinecarboxylate (650 mg, 3.3 mmol), and pyrrolidine (0.62 mL, 7.4 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 (250 mg, 27%).

Workup

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

Sources & evidence

ORD record
ord-c6922023240f4ff5918d2bf9e0d63344
Source dataset
uspto-grants-2002_11
Patent number
US06476051B2

Reaction notes

Loading…