Sodium Azide → HCID 57731931, compound

HRID 401797Notes

Reaction equation

HRID 401797 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[C@H:10]1[C@@H:14]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:13][O:12][CH2:11]1)(=O)=O>CS(C)=O.O>[N:1]([C@H:10]1[C@@H:14]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:13][O:12][CH2:11]1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86630784HCID 86630784, compound

Product 1

HCID 57731931HCID 57731931, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Sodium azide (30 g, 0.46 mol, 3.0 eq) was added under vigorous stirring to a mixture of compound (3S*,4S*)-4-(4-fluorophenyl)tetrahydrofuran-3-yl methanesulfonate (Preparation 60, 40 g, 0.15 mol, 1 eq) in dimethylsulfoxide (200 mL). The mixture was stirred on a water bath at 80 C for 4 h, cooled, diluted with water (700 mL), and extracted with ether (3×300 mL). The combined organic layer was washed with water (300 mL) and the saturated sodium chloride solution, dried over sodium sulfate, and rotary evaporated in the absence of vacuum at a bath temperature of 70° C. The residue was evaporated in water-aspirator vacuum at a bath temperature of 70° C. to give title compound (29.6 g, 0.14 mol, 94%).

Workup

  1. temperaturecooled
  2. extractionextracted with ether (3×300 mL)
  3. washThe combined organic layer was washed with water (300 mL)
  4. dry with materialthe saturated sodium chloride solution, dried over sodium sulfate
  5. customrotary evaporated in the absence of vacuum at a bath temperature of 70° C
  6. customThe residue was evaporated in water-aspirator vacuum at a bath temperature of 70° C.

Sources & evidence

ORD record
ord-243999e9405044a4b0019a37704b8782
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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