Phthalimide → trans-N-[3-(1H-pyrazol-1-yl)cyclopentyl]phthalimide

HRID 655150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655150
[N:1]1([C@@H:6]2[CH2:10][CH2:9][C@H:8](O)[CH2:7]2)[CH:5]=[CH:4][CH:3]=[N:2]1.[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[N:1]1([C@H:6]2[CH2:10][CH2:9][C@H:8]([N:16]3[C:15](=[O:17])[C:14]4=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]4[C:12]3=[O:22])[CH2:7]2)[CH:5]=[CH:4][CH:3]=[N:2]1

Komponenten

7

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 67133889cis-3-(1H-pyrazol-1-yl)cyclopentanol

Produkt 1

HCID 67133690trans-N-[3-(1H-pyrazol-1-yl)cyclopentyl]phthalimideAusbeute 52,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of cis-3-(1H-pyrazol-1-yl)cyclopentanol (5.01 g, 32.9 mmol) in THF (150 mL) was cooled to 0° C. and treated with phthalimide (5.33 g, 36.2 mmol), diisopropylazodicarboxylate (7.1 mL, 36.1 mmol) and triphenylphosphine (9.48 g, 36.1 mmol). The reaction mixture was stirred at 0° C. for 4 h. The reaction mixture was poured water and then extracted with EtOAc. The organic layer was dried over anhyd Na2SO4 followed by the removal of solvent. The crude product was purified by column chromatography (Chromatrex, Hexane/EtOAc=5/1) to yield trans-N-[3-(1H-pyrazol-1-yl)cyclopentyl]phthalimide (4.85 g, 52%) as a colorless powder.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhyd Na2SO4
  3. customfollowed by the removal of solvent
  4. customThe crude product was purified by column chromatography (Chromatrex, Hexane/EtOAc=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-ba091a7c1c0f4b9cbcd287eff98e2698
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071591B2

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