Pyrrolidine → HCID 18407062, compound

HRID 1016504Notes

Reaction equation

HRID 1016504 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]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:7]2[C:6]3[C:10](=[C:2]([Br:1])[CH:3]=[CH:4][CH:5]=3)[NH:9][CH:8]=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 27570207-Bromoindole

Product 1

HCID 18407062HCID 18407062, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 7-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 (215 mg, 29%).

Workup

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

Sources & evidence

ORD record
ord-e80f25d69d924ac186cde7f6ca2b1c78
Source dataset
uspto-grants-2002_11
Patent number
US06476051B2

Reaction notes

Loading…