Morpholine → 2-Methylhept-2-enoic acid

HRID 1650320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1650320
C(OC(N1CC(F)C[C@H]1C=C([C:16]1[CH2:22][C@H:21]2N([C:19](=O)[C@@H:20]2[C@H:23]([OH:25])C)[C:17]=1[C:27](OCC=C)=O)C)=O)C=C.N1CC[O:36]CC1.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>[CH3:19][C:20]([C:23]([OH:36])=[O:25])=[CH:21][CH2:22][CH2:16][CH2:17][CH3:27]

Komponenten

7

Edukt 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

Produkt 1

HCID 534110972-Methylhept-2-enoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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)-1hydroxyethyl]-7-oxo-1-azabicyclo 3.2.0]hept-2-ene-2carboxylic acid (248 mg).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-7e4eaef3f42d41b68ddd38ec7d77cf53
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04923857

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