Triphenylphosphine → HCID 117667319, compound

HRID 712764Notes

Reaction equation

HRID 712764 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8](=[O:10])[CH3:9])[CH2:4][CH2:3]1.[Br:11][C:12]1[CH:13]=[C:14](O)[CH:15]=[N:16][CH:17]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:11][C:12]1[CH:13]=[C:14]([O:1][CH:2]2[CH2:7][CH2:6][N:5]([C:8](=[O:10])[CH3:9])[CH2:4][CH2:3]2)[CH:15]=[N:16][CH:17]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5995293-Bromo-5-hydroxypyridineHCID 5363146Diisopropyl azodicarboxylateHCID 107492911-(4-Hydroxypiperidin-1-yl)ethan-1-one

Product 1

HCID 117667319HCID 117667319, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Hydroxy-piperidin-1-yl)-ethanone (200 mg 1.40 mmol) and 5-bromo-pyridin-3-ol (248 mg; 1.425 mmol) are added dropwise to a solution of PPh3 (606 mg) in THF (30 ml). DIAD (462 mg) is added to the solution. The mixture is stirred at room temperature overnight. The mixture is washed with water, diluted with DCM and dried over Na2SO4, filtered and concentrated to give 1-[4-(5-bromo-pyridin-3-yloxy)-piperidin-1-yl]-ethanone.

Workup

  1. washThe mixture is washed with water
  2. additiondiluted with DCM
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e8d5c09452854d56918062dfa5161a2a
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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