Sodium Azide → (2S)-1-Azido-3-[(2-chloro-3-pyridyl)oxy]propan-2-ol

HRID 1483026Notes

Reaction equation

HRID 1483026 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl:5][C:6]1[C:11]([O:12][CH2:13][C@@H:14]2[CH2:16][O:15]2)=[CH:10][CH:9]=[CH:8][N:7]=1.O.[N-]=[N+]=[N-].[Na+]>O.O1CCOCC1>[N:1]([CH2:16][C@H:14]([OH:15])[CH2:13][O:12][C:11]1[C:6]([Cl:5])=[N:7][CH:8]=[CH:9][CH:10]=1)=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 86609354Water sodium azideHCID 901347982-Chloro-3-[[(2S)-oxiran-2-yl]methoxy]pyridine

Product 1

HCID 90134929(2S)-1-Azido-3-[(2-chloro-3-pyridyl)oxy]propan-2-olYield 100.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
90 °C

Procedure

Dissolve sodium azide (22.84 g, 351.3 mmol) in water (195 mL). Separately, dissolve 2-chloro-3-[[(2S)-oxiran-2-yl]methoxy]pyridine (32.6 g, 175.6 mmol) in 1,4-dioxane (800 mL). Slowly add the water/sodium azide solution to the dioxane solution; heat to 90° C.; and stir for 1 hour. Cool the mixture and concentrate it under reduced pressure. Add water; extract with EtOAc (2×); combine the extracts; dry the combined extracts over Na2SO4; filter; and collect the filtrate. Remove the solvents under reduced pressure to provide the title compound (40.28 g, 92.8%) as a reddish white solid. MS (m/z): 229 (M+1).

Workup

  1. temperatureCool the mixture
  2. concentrationconcentrate it under reduced pressure
  3. extractionextract with EtOAc (2×)
  4. dry with materialdry the combined extracts over Na2SO4
  5. filtrationfilter
  6. customand collect the filtrate
  7. customRemove the solvents under reduced pressure

Sources & evidence

ORD record
ord-90e9b9594dc54193a325b8e5254554f7
Source dataset
uspto-grants-2016_08
Patent number
US09416138B2

Reaction notes

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