Methyl iodide → HCID 59278438, compound

HRID 1423050Notes

Reaction equation

HRID 1423050 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([Br:17])[CH:12]=1)[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].[CH3:19]I.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O>[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([Br:17])[CH:12]=1)[CH2:9][O:10][CH3:19])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 59278127HCID 59278127, compound

Product 1

HCID 59278438HCID 59278438, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [(R)-1-(2-bromopyridin-4-yl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester (180 mg, 0.57 mmol), methyl iodide (177 μL, 2.84 mmol) and tetrabutylammonium hydrogen sulfate (192 mg, 0.568 mmol) in THF (4.0 mL) is added 50% aqueous sodium hydroxide (2.5 mL). After 1 hour, the reaction mixture is diluted with water (50 mL) and extracted with ethyl ether (3×50 mL). The combined organic layers are dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with a gradient of 0-30% EtOAc in heptane to afford [(R)-1-(2-bromopyridin-4-yl)-2-methoxy-ethyl]-carbamic acid tert-butyl ester as oil which solidified upon standing.

Workup

  1. extractionextracted with ethyl ether (3×50 mL)
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by silica gel chromatography
  6. washeluting with a gradient of 0-30% EtOAc in heptane

Sources & evidence

ORD record
ord-8e87130be28a4570ba315245746b3035
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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