Ammonia → HCID 55297123, compound

HRID 401798Notes

Reaction equation

HRID 401798 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([C@H:23]1[C@@H:27]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH2:26][O:25][CH2:24]1)=[N+]=[N-].N.Cl>C1COCC1>[F:34][C:31]1[CH:32]=[CH:33][C:28]([C@H:27]2[CH2:26][O:25][CH2:24][C@H:23]2[NH2:20])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 57731931HCID 57731931, compound

Product 1

HCID 55297123HCID 55297123, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (45 g, 0.17 mol, 1.20 eq) was added in portions to a solution of compound (3S*,4R*)-3-azido-4-(4-fluorophenyl)tetrahydrofuran (Preparation 61, 29.6 g, 0.14 mol, 1 eq) in THF (200 mL) on a water bath under stirring for 1 h. The mixture was stirred at room temperature for 2 h, and ammonia 880 (50 mL) was added. The mixture was refluxed for 2 h and cooled. Then concentrated hydrogen chloride (13 mL) was added, and the mixture was evaporated. The residue was diluted with water (150 mL) and extracted with carbon tetrachloride (3×200 mL). Then the aqueous layer was alkalized with the saturated potassium carbonate solution and extracted with chloroform (3×200 mL). The combined organic layer was dried and evaporated to give title compound as a yellow oil (17.82 g, 0.1 mol, 69%).

Workup

  1. stirringThe mixture was stirred at room temperature for 2 h
  2. temperatureThe mixture was refluxed for 2 h
  3. temperaturecooled
  4. customthe mixture was evaporated
  5. additionThe residue was diluted with water (150 mL)
  6. extractionextracted with carbon tetrachloride (3×200 mL)
  7. extractionextracted with chloroform (3×200 mL)
  8. customThe combined organic layer was dried
  9. customevaporated

Sources & evidence

ORD record
ord-f3a362891b584903bdc95399246d7635
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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