Triphenylphosphine → N-Ethylphthalimide

HRID 982614

Reaktionsgleichung

Reaktionsgleichung von HRID 982614
ClC1C=CC=CC=1C1C(O)=NC2N=C(S(C)(=O)=O)N=CC=2C=1.O[CH2:24][CH2:25][N:26]1[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]2[C:27]1=[O:36].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCOCC1>[CH2:25]([N:26]1[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]2[C:27]1=[O:36])[CH3:24]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 77499N-(2-Hydroxyethyl)phthalimideHCID 5462977Diethyl azodicarboxylateHCID 178504840HCID 178504840, Verbindung

Produkt 1

HCID 21120N-EthylphthalimideAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a cooled (5° C.) suspension of 0.914 g (2.7 mmol) of 6-(chlorophenyl)-2-methanesulfonyl-pyrido[2,3-d]pyrimidin-7-ol, 1.041 g (5.4 mmol) of N-(2-hydroxyethyl)-phthalimide, 1.43 g (5.4 mmol) of triphenylphosphine in 15 mL of 1,4-dionxane was added dropwise a solution of 0.95 g (0.86 mL, 5.4 mmol) diethylazodicarboxylate in 5 mL of 1,4-dioxane over a period of 30 min. After addition was completed, the ice-water cooling bath was removed. The suspension soon turned into a clear light brown solution. This was allowed to stir at room temperature overnight. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on 120 g of silica gel using 90:10:0.5 ethyl acetate/dichloromethane/ammonium hydroxide to obtain 0.38 g of the N-ethylphthalimide intermediate. A mixture of 0.18 g (0.35 mmol) of this intermediate and 0.05 g (0.42 mmol) of trans-4-aminocyclohexanol in 1 mL of NMP was heated to 120° C. for 30 min. The reaction mixture was cooled, diluted with 75 mL of water and extracted with ethyl acetate (3×75 mL). The combined ethyl acetate solution was washed with water (3×75 mL), brine, dried, filtered and concentrated. The material was purified by column chromatography on 40 g of silica eluting with 5% methanol/dichloromethane affording 45 mg of compound 65. (mass spec. MH+=544, mp 208-210° C.).

Aufarbeitung

  1. temperatureTo a cooled
  2. additionAfter addition
  3. customthe ice-water cooling bath was removed
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. custompurified by column chromatography on 120 g of silica gel using 90:10:0.5 ethyl acetate/dichloromethane/ammonium hydroxide

Quellen und Nachweise

ORD-Eintrag
ord-cff5be102853419bb803ffefb8a2d074
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06861423B2

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