1,4-Bis(diphenylphosphino)butane → HCID 86598905, Verbindung

HRID 456752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456752
[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C@@H:10]1[C@H:15]2[CH2:16][C@H:12]([C@H:13]([OH:17])[CH2:14]2)[N:11]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:9])#[N:2].[C:25]1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)[CH:30]=CC=C[CH:26]=1.C(=O)(OCC)OCC=C>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[CH2:30]([O:17][C@H:13]1[C@H:12]2[CH2:16][C@H:15]([C@@H:10]([C:8]([N:4]3[CH2:5][CH2:6][CH2:7][C@H:3]3[C:1]#[N:2])=[O:9])[N:11]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1)[CH:25]=[CH2:26]

Komponenten

6

Edukt 3

HCID 821241,4-Bis(diphenylphosphino)butaneHCID 137020Allylethyl carbonateHCID 86598896tert-Butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate

Produkt 1

HCID 86598905HCID 86598905, VerbindungAusbeute 715,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of tert-butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate obtained in Example 5-7 (510 mg) in tetrahydrofuran (5.0 mL), were added 1,4-bis(diphenylphosphino)butane (64.8 mg), tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (39.3 mg) and allyl ethyl carbonate (0.4 mL). The mixture was stirred at 65° C. for 4 hrs. The resulting mixture was evaporated in vacuo and the residue was chromatographed on silica gel eluting with ethyl acetate to give the target compound (408 mg).

Aufarbeitung

  1. customThe resulting mixture was evaporated in vacuo
  2. customthe residue was chromatographed on silica gel eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-979686a2bd8849ac9d0f8a5ad53e7b93
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186731B2

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