Triphenylphosphine → 2-Methylhept-2-enoic acid

HRID 1650316Notes

Reaction equation

HRID 1650316 reaction equation
C(OC(N1CCC[C@H]1/C=C(/[C:15]1[CH2:21][C@H:20]2N([C:18](=O)[C@@H:19]2[C@H:22]([OH:24])C)[C:16]=1[C:26](OCC=C)=O)\C)=O)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC1(C)CC(=[O:58])CC(=O)C1>O1CCCC1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:18][C:19]([C:22]([OH:58])=[O:24])=[CH:20][CH2:21][CH2:15][CH2:16][CH3:26]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 31358DimedoneHCID 15702953allyl (5R,6S)-3-[(E)-2-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Product 1

HCID 534110972-Methylhept-2-enoic acidYield 163.2%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of allyl (5R,6S)-3-[(E)-2-{(2S)-1-allyloxycarbonylpyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (2.82 g) in a mixture of tetrahydrofuran (28 ml) and ethanol (14 ml) were added successively triphenylphosphine (0.51 g), 5,5-dimethyl-1,3cyclohexanedione (dimedone) (1.79 g), and tetrakis-(triphenylphosphine) palladium (0) (220 mg). Stirring at ambient temperature for 1 hour gave a precipitate, which was collected by filtration, washed with tetrahydrofuran (40 ml) and dissolved in water (150 ml). The solution was washed with ethyl acetate (50 ml×2), concentrated in vacuo and lyophilized to give (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(E)-2-(2S)-pyrrolidin-2-yl}-1-methylethenyl]-1-azabicyclo[b 3.2.0]hept-2-ene-2-carboxylic acid (1.52 g).

Workup

  1. customgave a precipitate, which
  2. filtrationwas collected by filtration
  3. washwashed with tetrahydrofuran (40 ml)
  4. dissolutiondissolved in water (150 ml)
  5. washThe solution was washed with ethyl acetate (50 ml×2)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-116e5ee664d047bf970169ab51c3b2a6
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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