N-Bromoacetamide → 6-Bromo-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-yl acetate

HRID 1099166

Reaktionsgleichung

Reaktionsgleichung von HRID 1099166
[Br:1]NC(=O)C.[CH:6]([Si:9]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:10][CH:11]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[CH:15]=[CH:14][CH2:13][CH2:12]1)([CH3:8])[CH3:7].[C:28]([O-:31])(=[O:30])[CH3:29].[Li+]>CC(O)=O>[C:28]([O:31][CH:15]1[C:16]2[C:17](=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:11]([O:10][Si:9]([CH:6]([CH3:8])[CH3:7])([CH:22]([CH3:24])[CH3:23])[CH:25]([CH3:27])[CH3:26])[CH2:12][CH2:13][CH:14]1[Br:1])(=[O:30])[CH3:29]

Komponenten

5

Edukt 3

HCID 4353N-BromoacetamideHCID 3474584Lithium acetateHCID 57911494(Z)-9-(Triisopropylsilyloxy)-8,9-dihydro-7H-cyclohepta[b]pyridine

Produkt 1

HCID 579114096-Bromo-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-yl acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

N-bromoacetamide (2.021 g, 14.65 mmol) was added to the AcOH (100 mL) suspension of (Z)-9-(triisopropylsilyloxy)-8,9-dihydro-7H-cyclohepta[b]pyridine (4.5597 g, 14.36 mmol) and LITHIUM ACETATE (3.79 g, 57.4 mmol) at rt under N2. The flask was wrapped with alumina foil and stirred at room temperature overnight. The reaction became a clear yellow solution. The solvent was evaporated via high vacuum. The crude was partitioned between water and ethyl acetate. Na2CO3 was added until no bubbling. The organic was separated and the aqueous was extract by ethyl acetate again. The combined organic layer was dried (Na2SO4), filtered and concentrated to give a tan oil (crude product: 6.37 g). The crude was used as it is. MS (ESI)[M+H+]=458.36.

Aufarbeitung

  1. customThe solvent was evaporated via high vacuum
  2. customThe crude was partitioned between water and ethyl acetate
  3. additionNa2CO3 was added until no bubbling
  4. customThe organic was separated
  5. extractionthe aqueous was extract by ethyl acetate again
  6. dry with materialThe combined organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a tan oil (crude product: 6.37 g)

Quellen und Nachweise

ORD-Eintrag
ord-28af8d81559a4920a5df1a907b25731b
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143403B2

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