Tetrahydrofuran → 1-(6-(2-(4-Fluorophenyl)-2-methylpropylamino)pyridin-3-yl)ethane-1,2-diol

HRID 2276754Notes

Reaction equation

HRID 2276754 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:20])([CH3:19])[CH2:9][NH:10][C:11]2[CH:16]=CC(C=C)=[CH:13][N:12]=2)=[CH:4][CH:3]=1.[NH+]1([O-])CC[O:24]CC1.[CH2:28]1[CH2:32][O:31][CH2:30][CH2:29]1>C1COCC1.O.O.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:20])([CH3:19])[CH2:9][NH:10][C:11]2[N:12]=[CH:13][C:29]([CH:28]([OH:24])[CH2:32][OH:31])=[CH:30][CH:16]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 15900019Morpholine oxideHCID 67452625N-(2-(4-fluorophenyl)-2-methylpropyl)-5-vinylpyridin-2-amine

Product 1

HCID 545920171-(6-(2-(4-Fluorophenyl)-2-methylpropylamino)pyridin-3-yl)ethane-1,2-diolYield 86%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

N-(2-(4-fluorophenyl)-2-methylpropyl)-5-vinylpyridin-2-amine (158 mg, 0.6 mmol, 1.0 equiv) was added to a foil-covered 20 dram vial and then dissolved in a 50% THF/water mixture (6 mL). Osmium tetraoxide (15 mg, 0.06 mmol, 0.1 equiv) and morpholine N-oxide (103 mg, 0.9 mmol, 1.5 equiv) were added, and the reaction was stirred for 1 h. Additional THF (3 mL) was added, and the reaction was stirred for 3 h. The reaction mixture was then diluted with water (10 mL) and extracted with ethyl acetate (30 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to give a crude solid that was purified by reverse phase column chromatography to give 129 mg (86%) of 1-(6-(2-(4-fluorophenyl)-2-methylpropylamino)pyridin-3-yl)ethane-1,2-diol (m/z [M+H]=305).

Workup

  1. stirringthe reaction was stirred for 3 h
  2. extractionextracted with ethyl acetate (30 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude solid that
  7. customwas purified by reverse phase column chromatography

Sources & evidence

ORD record
ord-d3f78cd64be54f60a02f1bddbc3983c4
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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