Triphenylphosphine → HCID 22107128, compound

HRID 1900614Notes

Reaction equation

HRID 1900614 reaction equation
C[C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][CH:5]([C:12]([OH:14])=O)[CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8].[C:19]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:38][C:39]1[CH:40]=C2C(=[CH:47][CH:48]=1)C=C(O)C=C2.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[Br:38][C:39]1[CH:40]=[C:17]2[C:18](=[CH:47][CH:48]=1)[CH:2]=[C:3]([O:4][CH:5]1[CH2:6][CH:7]([C:9]([O:11][CH3:19])=[O:10])[NH:8][C:12]1=[O:14])[CH:15]=[CH:16]2

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 271446-Bromo-2-naphthalenolHCID 5462977Diethyl azodicarboxylateHCID 54262066HCID 54262066, compound

Product 1

HCID 22107128HCID 22107128, compoundYield 108.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of the compound prepared as described in Example 4 (0.498 g), triphenylphosphine (0.932 g), and 6-bromo-2-naphthol (0.793 g) in tetrahydrofuran (4.3 ml) was cooled to approximately 1°-2° C., and treated with a solution of diethylazodicarboxylate (0.619 g) in tetrahydrofuran (4.3 ml) over a one minute period. After the addition was complete, the reaction was allowed to warm to room temperature. After about 23 hours, the solution was concentrated in vacuo. The residue was diluted with chloroform (2 ml), the insoluble material removed by filtration, and the filtrate concentrated in vacuo. The oil was dissolved in methylene chloride and purified by preparative centrifugal thin-layer chromatography (4 mm plate, flow rate=8 ml/min), eluting with ethyl acetate/hexane (1:1) until first band elutes then solvent switched to hexane:ethyl acetate (1:3). The fractions containing the title compound were combined, dried over magnesium sulfate, filtered and concentrated in vacuo to give methyl 3-(6-bromo-2-naphthyloxy)-2-pyrrolidone-5-carboxylate (778 mg).

Workup

  1. additionA mixture of the compound
  2. customprepared
  3. temperaturewas cooled to approximately 1°-2° C.
  4. additionAfter the addition
  5. concentrationthe solution was concentrated in vacuo
  6. additionThe residue was diluted with chloroform (2 ml)
  7. customthe insoluble material removed by filtration
  8. concentrationthe filtrate concentrated in vacuo
  9. dissolutionThe oil was dissolved in methylene chloride
  10. custompurified by preparative centrifugal thin-layer chromatography (4 mm plate, flow rate=8 ml/min)
  11. washeluting with ethyl acetate/hexane (1:1) until first band elutes
  12. additionThe fractions containing the title compound
  13. dry with materialdried over magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06b42e4693b0470a89fd1cc805c78045
Source dataset
uspto-grants-1996_11
Patent number
US05576323

Reaction notes

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