Morpholine → (5R,6S)-3-[2-{(2S)-4-fluoropyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

HRID 1090552Notes

Reaction equation

HRID 1090552 reaction equation
C(OC([N:7]1[CH2:11][CH:10]([F:12])[CH2:9][C@H:8]1[CH:13]=[C:14]([C:16]1[CH2:22][C@H:21]2[N:18]([C:19](=[O:26])[C@@H:20]2[C@H:23]([OH:25])[CH3:24])[C:17]=1[C:27]([O:29]CC=C)=[O:28])[CH3:15])=O)C=C.N1CCOCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>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>[F:12][CH:10]1[CH2:11][NH:7][C@H:8]([CH:13]=[C:14]([C:16]2[CH2:22][C@H:21]3[N:18]([C:19](=[O:26])[C@@H:20]3[C@H:23]([OH:25])[CH3:24])[C:17]=2[C:27]([OH:29])=[O:28])[CH3:15])[CH2:9]1

Participants

7

Reactant 3

HCID 8083MorpholineHCID 11776TriphenylphosphineHCID 86743911allyl (5R,6S)-3-[2-{(2S)-1-allyloxycarbonyl-4-fluoropyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Product 1

HCID 57167763(5R,6S)-3-[2-{(2S)-4-fluoropyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidYield 20.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of allyl (5R,6S)-3-[2-{(2S)-1-allyloxycarbonyl-4-fluoropyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (1.7 g), morpholine (694 μl), and triphenylphosphine (199 mg) in tetrahydrofuran (30 ml) and ethanol (10 ml) was added tetrakis(triphenylphosphine)palladium(0) (263 mg) at room temperature. After stirring for an hour, the precipitate was filtered, washed in turn with dichloromethane (3 times) and acetone (twice), and dried under reduced pressure to give (5R,6S)-3-[2-{(2S)-4-fluoropyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (248 mg).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed in turn with dichloromethane (3 times) and acetone (twice), and
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-ec6882b228a34a4d8e7b781cd6aecb93
Source dataset
uspto-grants-1992_01
Patent number
US05081237

Reaction notes

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