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Benzyl Alcohol → Benzyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

HRID 881739
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 881739
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]34[CH2:21][CH2:20][C:17]([CH2:22][C:23]([O:25][CH3:26])=[O:24])([CH2:18][CH2:19]3)[O:16][CH2:15]4)=[CH:10][CH:9]=2)=[N:6][CH:7]=1.C(O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]34[CH2:19][CH2:18][C:17]([CH2:22][C:23]([O:25][CH2:26][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)=[O:24])([CH2:20][CH2:21]3)[O:16][CH2:15]4)=[CH:12][CH:13]=2)=[N:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 244Benzyl AlcoholHCID 86700825Methyl2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Produkt 1

HCID 86700842Benzyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetateAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11026Titanium isopropoxideKatalysator

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a mixture of methyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (286 mg, 0.812 mmol) in neat benzyl alcohol (6 mL, 57.9 mmol) was added titanium(IV) isopropoxide (1.5 mL, 5.12 mmol) and 4 A molecular sieves (5 g, 0.812 mmol). The reaction mixture was heated at 130° C. overnight. The reaction was quenched by saturated NaHCO3 and was extracted with EtOAc. The combined organic layer was filtered and washed with brine and dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by prep-HPLC (15 to 90% ACN-water (0.1% NH4OH) with X-bridge C18 column) to give the title compound after drying (150 mg, 43% yield). LC/MS, ESI-MS(+): 429.1, RT: 1.41 (Condition E).

Aufarbeitung

  1. customThe reaction was quenched by saturated NaHCO3
  2. extractionwas extracted with EtOAc
  3. filtrationThe combined organic layer was filtered
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by prep-HPLC (15 to 90% ACN-water (0.1% NH4OH) with X-bridge C18 column)

Quellen und Nachweise

ORD-Eintrag
ord-1c8cb50d6f2a4ba1a723b64c8b603d5d
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08993619B2

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