Tetrahydrofuran → HCID 67974700, Verbindung

HRID 2046196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2046196
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH:7]([CH3:27])[CH2:8][N:9]1[CH2:14][CH2:13][N:12]2[N:15]=[C:16]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:17]=[C:11]2[C:10]1=[O:26])(C)(C)C.C1COCC1>CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[OH:6][CH:7]([CH3:27])[CH2:8][N:9]1[CH2:14][CH2:13][N:12]2[N:15]=[C:16]([CH2:18][O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:17]=[C:11]2[C:10]1=[O:26]

Komponenten

4

Edukt 2

HCID 8028TetrahydrofuranHCID 70654271HCID 70654271, Verbindung

Produkt 1

HCID 67974700HCID 67974700, VerbindungAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2724141Tetrabutylammonium FluorideLösungsmittel

Versuchsvorschrift

(Rac)-5-[2-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (70 mg, 0.13 mmol) was dissolved in a 1M solution of TBAF in THF (0.13 mL, 0.13 mmol). The mixture stirred at room temperature for 16 hours. Then the solvent was evaporated in vacuo to yield a yellow crude that was purified by flash column chromatography (silica; MeOH in DCM from 0/100 to 10/90) to yield (rac)-5-(2-hydroxy-propyl)-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (20 mg, 51% yield) as a white solid.

Aufarbeitung

  1. customThen the solvent was evaporated in vacuo
  2. customto yield a yellow crude that
  3. customwas purified by flash column chromatography (silica; MeOH in DCM from 0/100 to 10/90)

Quellen und Nachweise

ORD-Eintrag
ord-14cc64d5479142948c9aa7833c734482
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592422B2

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