Sodium Azide → 3-Azidomethyl-2-(5-bromopyridin-3-yl)-2-azabicyclo[3.1.0]hexane

HRID 241602Notes

Reaction equation

HRID 241602 reaction equation
CS(O[CH2:6][CH:7]1[CH2:12][CH:11]2[CH:9]([CH2:10]2)[N:8]1[C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=1)(=O)=O.[N-:20]=[N+:21]=[N-:22].[Na+]>CC1C=COC=1C.CCOCC>[N:20]([CH2:6][CH:7]1[CH2:12][CH:11]2[CH:9]([CH2:10]2)[N:8]1[C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=1)=[N+:21]=[N-:22]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 866749142-(5-Bromopyridin-3-yl)-2-azabicyclo[3.1.0]hex-3-ylmethyl methanesulfonate

Product 1

HCID 711149553-Azidomethyl-2-(5-bromopyridin-3-yl)-2-azabicyclo[3.1.0]hexaneYield 90%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 343372,3-DimethylfuranSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of methane sulfonate (as obtained in Step (i) of Example 1) (215 mg, 0.62 mmol) in dry dimethylfuran (2 mL) was added sodium azide (180 mg, 2.77 mmol). The reaction mixture was gradually heated to 90° C. and stirred for 16 hours. Upon completion of the reaction, it was diluted with ether, washed with water, brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude product was purified by silica gel flash column chromatography to obtain the title compound as gummy liquid of 164 mg. Yield: 90%.

Workup

  1. customUpon completion of the reaction, it
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-787b1c2a609141ca87f2385f22b1179f
Source dataset
uspto-grants-2014_02
Patent number
US08653071B2

Reaction notes

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