Triphenylphosphine → (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(E)-2-{(2S)-pyrrolidin-2-yl}-1-methylethenyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

HRID 1090548Notes

Reaction equation

HRID 1090548 reaction equation
C(OC([N:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1/[CH:12]=[C:13](/[C:15]1[CH2:21][C@H:20]2[N:17]([C:18](=[O:25])[C@@H:19]2[C@H:22]([OH:24])[CH3:23])[C:16]=1[C:26]([O:28]CC=C)=[O:27])\[CH3:14])=O)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC1(C)CC(=O)CC(=O)C1>O1CCCC1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:24][C@@H:22]([C@H:19]1[C:18](=[O:25])[N:17]2[C@@H:20]1[CH2:21][C:15](/[C:13](/[CH3:14])=[CH:12]/[C@@H:8]1[CH2:9][CH2:10][CH2:11][NH:7]1)=[C:16]2[C:26]([OH:28])=[O:27])[CH3:23]

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 10086476(5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(E)-2-{(2S)-pyrrolidin-2-yl}-1-methylethenyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidYield 75.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 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-1,3-cyclohexanedione (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[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-a5a3f1d5dc5c48a2aa41f2fd4d33bacf
Source dataset
uspto-grants-1992_01
Patent number
US05081237

Reaction notes

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