Triphenylphosphine → HCID 22107148, compound

HRID 1900624Notes

Reaction equation

HRID 1900624 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.[C:38]1([CH2:44][CH2:45][CH2:46][CH2:47]C2C=CC(O)=CC=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:38]1([CH2:44][CH2:45][CH2:46][CH2:47][C:17]2[CH:18]=[CH:2][C:3]([O:4][CH:5]3[CH2:6][CH:7]([C:9]([O:11][CH3:19])=[O:10])[NH:8][C:12]3=[O:14])=[CH:15][CH:16]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 14086163HCID 14086163, compoundHCID 54262066HCID 54262066, compound

Product 1

HCID 22107148HCID 22107148, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the compound prepared as described in Example 4 (0.434 g), triphenylphosphine (0.8113 g), and 4-(4-phenylbutyl)phenol (0.700 g) in tetrahydrofuran (3.8 ml) was cooled to approximately 1°-2° C., and treated with diethylazodicarboxylate (0.5386 g) over a two 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 (1 ml), the insoluble material removed by filtration, and the filtrate concentrated in vacuo. The residual oil was dissolved in methylene chloride (4 ml) and purified by preparative centrifugal thin-layer chromatography (4 mm plate, flow rate=8 ml/min), eluting with 50% ethyl acetate/hexane until first band elutes then solvent switched to 100% ethyl acetate. The fractions containing the desired compound were combined, dried over magnesium sulfate, filtered and concentrated in vacuo to give methyl 3-[4-(4-phenylbutyl)phenoxy]-2-pyrrolidone-5-carboxylate (583 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 (1 ml)
  7. customthe insoluble material removed by filtration
  8. concentrationthe filtrate concentrated in vacuo
  9. dissolutionThe residual oil was dissolved in methylene chloride (4 ml)
  10. custompurified by preparative centrifugal thin-layer chromatography (4 mm plate, flow rate=8 ml/min)
  11. washeluting with 50% ethyl acetate/hexane until first band elutes
  12. additionThe fractions containing the desired compound
  13. dry with materialdried over magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a99e89c3f7764f7eb04c1e2c45e81293
Source dataset
uspto-grants-1996_11
Patent number
US05576323

Reaction notes

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