Methanol → HCID 69471455, compound

HRID 1374454Notes

Reaction equation

HRID 1374454 reaction equation
[I:1][CH:2]1[CH2:7][CH2:6][NH:5][CH:4]([C:8]([OH:10])=[O:9])[CH2:3]1.[CH3:11]O>S(=O)(=O)(O)O>[CH3:11][O:9][C:8](=[O:10])[CH:4]1[CH2:3][CH:2]([I:1])[CH2:7][CH2:6][NH:5]1

Participants

4

Reactant 2

HCID 887MethanolHCID 21076079HCID 21076079, compound

Product 1

HCID 69471455HCID 69471455, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of 13a prepared in general method Q (5 g, 13.26 mmol) in methanol (500 mL) was added a few drops of conc. sulfuric acid. The reaction mixture was refluxed overnight. The solvent was evaporated and the residue was purified by chromatography to give 4-iodopipecolinic acid methyl ester 14a as a yellow solid (3.0 g, 86%): 1H NMR (300 MHz, CDCl3) δ 8.49 (d, J=1.5, 1), 8.37 (d, J=5.4, 1), 7.85 (dd, J=1.6, 5.2, 1), 4.00 (s, 3); MS (ESPOS): 264.3 [M+H]+.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-d39b5ac8db784782b46956a0f5784bd2
Source dataset
uspto-grants-2007_01
Patent number
US07164011B2

Reaction notes

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