Ammonium → HCID 118417129, compound

HRID 1483044Notes

Reaction equation

HRID 1483044 reaction equation
[N:1]([CH2:4][C@H:5]1[CH2:10][O:9][C@H:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][O:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1COCC1.[NH4+]>O>[C:11]1([C@@H:8]2[CH2:7][O:6][C@@H:5]([CH2:4][NH2:1])[CH2:10][O:9]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 223AmmoniumHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 90134882HCID 90134882, compound

Product 1

HCID 118417129HCID 118417129, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine trans-2-azidomethyl-5-phenyl-1,4-dioxane (319 mg, 1.46 mmol), triphenylphosphine (765 mg, 2.92 mmol), and THF (20 mL) and H2O (5 mL). Stir the reaction mixture at room temperature overnight. Add Dowex AG 50W-X8 cation exchange resin (ammonium form, 200-400 mesh, 1 g) to the reaction and stir at ambient temperature for 20 minutes. Filter and sequentially wash the resin with THF (10 mL) then H2O (10 mL). Elute by rinsing the SCX resin with NH3 in MeOH (120 mL 7N) and concentrate the filtrate under reduced pressure to provide the title compound (280 mg, 99.6%) as a colorless oil. MS (m/z): 194 (M+1).

Workup

  1. stirringstir at ambient temperature for 20 minutes
  2. filtrationFilter
  3. washsequentially wash the resin with THF (10 mL)
  4. washElute
  5. washby rinsing the SCX resin with NH3 in MeOH (120 mL 7N)
  6. concentrationconcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-bc6fcab56fa343a6a65e833c5425acc2
Source dataset
uspto-grants-2016_08
Patent number
US09416138B2

Reaction notes

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