Potassium Carbonate → HCID 64115555, compound

HRID 1392902Notes

Reaction equation

HRID 1392902 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[OH:10][C@H:11]1[CH2:15][CH2:14][NH:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][N:13]2[CH2:14][CH2:15][C@H:11]([OH:10])[CH2:12]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 2733874(3S)-pyrrolidin-3-ol

Product 1

HCID 64115555HCID 64115555, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine (1.0 g, 6.2 mmole) in 10 mL of dry acetonitrile is added 1.03 mL (12.4 mmol) of (S)-3-hydroxy-pyrrolidine followed by 858 mg (6.2 mmol) of potassium carbonate. The reaction is heated at 80° C. for 2 h. After cooling, the reaction mixture is quenched with 20 mL of water, extracted three-times with methylene chloride, and dried over sodium sulfate. Concentration of the solvent provided an oil which was purified by silica gel chromatography to provide 900 mg (68% yield) of (S)-1-(6-Chloro-pyridin-3-ylmethyl)-pyrrolidin-3-ol. Diagnostic C13 NMR (100 MHz, CDCl3) 35.1, 52.5, 56.7, 63.0, 71.4, 124.2, 133.4, 139.6, 149.9, 150.4; MS 213.2 (M+H).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture is quenched with 20 mL of water
  3. extractionextracted three-times with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. customConcentration of the solvent provided an oil which
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-6b28e8e0c5aa4b7ca044acbaf193b5c2
Source dataset
uspto-grants-2008_03
Patent number
US07345038B2

Reaction notes

Loading…