Pyrrolidine → 3-[1-(t-Butoxycarbonyl)-1,2,3,6-tetrahydro-4-pyridinyl]-7-fluoroindole

HRID 1016500Notes

Reaction equation

HRID 1016500 reaction equation
[F: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]([F: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 27745047-Fluoro-1H-indole

Product 1

HCID 184070743-[1-(t-Butoxycarbonyl)-1,2,3,6-tetrahydro-4-pyridinyl]-7-fluoroindoleYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 7-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 (620 mg, 66%).

Workup

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

Sources & evidence

ORD record
ord-fb1f4423f6b64a30ab3c5e59e911692e
Source dataset
uspto-grants-2002_11
Patent number
US06476051B2

Reaction notes

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