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2-Amino-5-cyanopyridine → (S)-3-(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)-N-(5-cyanopyridin-2-yl)-2-hydroxypropanamide

HRID 1098272
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1098272
C[Al](C)C.[NH2:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1.[Si:14]([O:21][CH:22]1[CH2:25][N:24]([CH2:26][C@H:27]([OH:32])[C:28](OC)=[O:29])[CH2:23]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C1(C)C=CC=CC=1>[Si:14]([O:21][CH:22]1[CH2:25][N:24]([CH2:26][C@H:27]([OH:32])[C:28]([NH:5][C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=2)=[O:29])[CH2:23]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]
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Komponenten

5

Edukt 3

HCID 8182602-Amino-5-cyanopyridine2×HCID 16682925TrimethylaluminumHCID 57504648(S)-methyl 3-(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)-2-hydroxypropanoate

Produkt 1

HCID 57504736(S)-3-(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)-N-(5-cyanopyridin-2-yl)-2-hydroxypropanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Trimethylaluminium (7.95 mL, 15.89 mmol) was added to 6-aminonicotinonitrile (1.646 g, 13.82 mmol) in toluene (50 mL) cooled to 0° C. under nitrogen. The resulting solution was stirred at 0° C. for 10 minutes. (S)-Methyl 3-(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)-2-hydroxypropanoate (Intermediate AD3) (4.0 g, 13.82 mmol) in toluene (20 mL) was added and the resulting solution was allowed to warm to room temperature and then heated at 60° C. for 3 hours. The mixture was cooled to ˜10° C. and quenched by the addition of 20% Rochelle salt solution. It was then diluted with EtOAc (50 mL) and stirred for 2 hours. The organic phase was separated, washed with water and brine, dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography on silica with EtOAc as eluent to afford the product containing some 6-aminonicotinonitrile (4.1 g). This was used without further purification.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. temperatureheated at 60° C. for 3 hours
  3. temperatureThe mixture was cooled to ˜10° C.
  4. customquenched by the addition of 20% Rochelle salt solution
  5. additionIt was then diluted with EtOAc (50 mL)
  6. stirringstirred for 2 hours
  7. customThe organic phase was separated
  8. washwashed with water and brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was purified by flash chromatography on silica with EtOAc as eluent
  13. customto afford the product
  14. customThis was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-8366d5cbdf7f4d3bbd258dfb9a4daa9a
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08143263B2

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