Triphenylphosphine → HCID 59603080, compound

HRID 2068697Notes

Reaction equation

HRID 2068697 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:34]([N:41]1[CH2:45][CH2:44][CH:43](O)[CH2:42]1)([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].[Br:47][C:48]1[CH:53]=[CH:52][N:51]=[C:50]([OH:54])[CH:49]=1>C1COCC1.O>[Br:47][C:48]1[CH:53]=[CH:52][N:51]([CH:43]2[CH2:44][CH2:45][N:41]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:42]2)[C:50](=[O:54])[CH:49]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 44169391-Boc-3-pyrrolidinolHCID 5363146Diisopropyl azodicarboxylateHCID 178515446HCID 178515446, compound

Product 1

HCID 59603080HCID 59603080, compoundYield 109.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold solution of triphenylphosphine (0.17 g, 0.63 mmol) in THF (10.0 mL) was added DIAD (0.12 mL, 0.63 mmol) and the resulting solution was stirred at the same temperature for 15 min. after which a yellow precipitate was formed. 1-Boc-3-hydroxypyrrolidine (0.10 g, 0.53 mmol) was then added to the reaction mixture and allowed to stir for 20 min followed by addition of 4-bromo-2-hydroxypyridine (0.093 g, 0.53 mmol). The resulting reaction mixture was stirred for 16 h at room temperature. After completion of reaction (TLC monitoring), the reaction mixture was diluted with water and extracted with EtOAc (3×50 ml). The combined organics was dried (Na2SO4), filtered and concentrated. The residue was purified over silica gel (100-200 M, 0.5% MeOH-DCM) to obtain the desired product (0.20 g, quantitative yield). MS: 343.10 (M+H)+.

Workup

  1. customwas formed
  2. stirringto stir for 20 min
  3. customThe resulting reaction mixture
  4. stirringwas stirred for 16 h at room temperature
  5. customAfter completion of reaction (TLC monitoring)
  6. extractionextracted with EtOAc (3×50 ml)
  7. dry with materialThe combined organics was dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified over silica gel (100-200 M, 0.5% MeOH-DCM)

Sources & evidence

ORD record
ord-a1fdee770d0042a0b163f103cc197982
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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