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

HRID 1029687Notes

Reaction equation

HRID 1029687 reaction equation
C(OC([N:7]1[CH2:11][CH2:10][CH:9]([C:12]2[CH2:18][C@H:17]3[N:14]([C:15](=[O:22])[C@@H:16]3[C@H:19]([OH:21])[CH3:20])[C:13]=2[C:23]([O:25]CC=C)=[O:24])[CH2:8]1)=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:21][C@@H:19]([C@H:16]1[C:15](=[O:22])[N:14]2[C@@H:17]1[CH2:18][C:12]([CH:9]1[CH2:10][CH2:11][NH:7][CH2:8]1)=[C:13]2[C:23]([OH:25])=[O:24])[CH3:20]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 31358DimedoneHCID 15117368allyl (5R,6S)-3-(1-allyloxycarbonylpyrrolidin-3-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Product 1

HCID 15117376(5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-(pyrrolidin-3-yl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidYield 74.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of allyl (5R,6S)-3-(1-allyloxycarbonylpyrrolidin-3-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.94 g) in a mixture of tetrahydrofuran (14 ml) and ethanol (2 ml) were added successively triphenylphosphine (130 mg), 5,5-dimethyl-1,3-cyclohexanedione (dimedone) (0.66 g) and tetrakis(triphenylphosphine)palladium(0) (280 mg). Stirring at ambient temperature for 1 hour gave a precipitate, which was collected by filtration and washed with tetrahydrofuran to give (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-(pyrrolidin-3-yl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (480 mg).

Workup

  1. customgave a precipitate, which
  2. filtrationwas collected by filtration
  3. washwashed with tetrahydrofuran

Sources & evidence

ORD record
ord-9a0790a8ed604c678a1b4780aa73862d
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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