Sodium hydride → HCID 90134886, compound

HRID 1483027Notes

Reaction equation

HRID 1483027 reaction equation
[N:1]([CH2:4][C@H:5]([OH:15])[CH2:6][O:7][C:8]1[C:9](Cl)=[N:10][CH:11]=[CH:12][CH:13]=1)=[N+:2]=[N-:3].[H-].[Na+]>C1COCC1>[N:1]([CH2:4][C@@H:5]1[O:15][C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[O:7][CH2:6]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 90134929(2S)-1-Azido-3-[(2-chloro-3-pyridyl)oxy]propan-2-ol

Product 1

HCID 90134886HCID 90134886, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

Dissolve (2S)-1-azido-3-[(2-chloro-3-pyridyl)oxy]propan-2-ol (40.28 g, 176.17 mmol) in THF (880 mL) and slowly add sodium hydride (60% dispersion in mineral oil; 14.09 g, 352.35 mmol). Heat the mixture to 90° C. and stir for 2 hours at that temperature. Slowly pour the mixture into 1 liter of packed ice to quench the reaction. Remove the dioxanes under reduced pressure and extract the resulting mixture with EtOAc (3×). Dry the combined extracts over Na2SO4; filter; and concentrate the filtrate under reduced pressure. Purify via flash column chromatography using 2×330 g silica gel, eluting with a gradient of 0-75% of Et2O in hexanes. Combine the product fractions and remove solvents under reduced pressure to provide the title compound as a yellow solid (7.5 g., 22.15%). MS (m/z): 193 (M+1).

Workup

  1. customto quench
  2. customthe reaction
  3. customRemove the dioxanes under reduced pressure
  4. extractionextract the resulting mixture with EtOAc (3×)
  5. dry with materialDry the combined extracts over Na2SO4
  6. filtrationfilter
  7. concentrationand concentrate the filtrate under reduced pressure
  8. customPurify via flash column chromatography
  9. washeluting with a gradient of 0-75% of Et2O in hexanes
  10. customCombine the product fractions and remove solvents under reduced pressure

Sources & evidence

ORD record
ord-a560e180128f4f5d85ed0f58e26979c6
Source dataset
uspto-grants-2016_08
Patent number
US09416138B2

Reaction notes

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