Triphenylphosphine → HCID 68939021, compound

HRID 749251Notes

Reaction equation

HRID 749251 reaction equation
[N:1]([CH2:4][C@@H:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:9]([F:21])[CH:8]=1)[OH:6])=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[NH2:1][CH2:4][C@@H:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:9]([F:21])[CH:8]=1)[OH:6]

Participants

5

Reactant 2

HCID 11776Triphenylphosphine2×HCID 86605117HCID 86605117, compound

Product 1

HCID 68939021HCID 68939021, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (1R)-2-azido-1-[4-(benzyloxy)-3-fluorophenyl]ethanol (410 mg) in THF (8 mL) and water (2 mL) was treated with PPh3 (410 mg) and stirred for 1 h prior to addition of further with PPh3 (220 mg). After stirring for a further 4 h the reaction mixture was concentrated in vacuo and the residue partitioned between EtOAc and water. The organic phase was washed three times with 5% NaHCO3(aq) dried and concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with DCM, 1% MeOH in DCM, 2% MeOH in DCM, 5% MeOH containing 0.5% Et3N in DCM, and finally 20% MeOH containing 1% Et3N in DCM) to give the title compound (260 mg). LCMS RT=2.16 min.

Workup

  1. stirringAfter stirring for a further 4 h the reaction mixture
  2. concentrationwas concentrated in vacuo
  3. customthe residue partitioned between EtOAc and water
  4. washThe organic phase was washed three times with 5% NaHCO3(aq)
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel
  8. washeluting with DCM, 1% MeOH in DCM, 2% MeOH in DCM

Sources & evidence

ORD record
ord-4d630906455f44d7bc6f243bbd5d86b7
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

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