N-bromobutanimide → (S)-1-(5-Bromo-6-methoxypyridin-2-yl)pyrrolidin-3-ol

HRID 1054904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1054904
[CH3:1][O:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10]2)[CH:6]=[CH:5][CH:4]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:15][C:4]1[CH:5]=[CH:6][C:7]([N:9]2[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10]2)=[N:8][C:3]=1[O:2][CH3:1]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 86698868(3S)-1-(6-methoxypyridin-2-yl)pyrrolidin-3-ol

Produkt 1

HCID 86698869(S)-1-(5-Bromo-6-methoxypyridin-2-yl)pyrrolidin-3-olAusbeute 8,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
8 °C

Versuchsvorschrift

To a solution of (3S)-1-(6-methoxypyridin-2-yl)pyrrolidin-3-ol (1.6 g, 8.24 mmol) in chloroform (90 mL), was added N-bromosuccinimide (1.47 g, 8.24 mmol) at 0° C. with an ice bath. The reaction was allowed to stir at room temperature (8° C.) for 5 hour. TLC (petroleum ether/ethyl acetate) showed that the reaction was complete. The reaction mixture was evaporated to remove chloroform, dissolved in DCM (20 mL) and diluted with water (15 mL). The resulting mixture was separated and the aqueous phase was extracted with dichloromethane (25 mL*3). The combined organic phase was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether, 0-25% to give the title compound (187 mg, 8.5%) as a yellow gum. 1H NMR (400 MHz, CDCl3) ppm 7.46 (d, 1 H) 5.77 (d, 1 H) 4.44-4.59 (m, 1 H) 3.92 (s, 3 H) 3.37-3.61 (m, 4 H) 1.96-2.24 (m, 3 H).

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. customto remove chloroform
  3. dissolutiondissolved in DCM (20 mL)
  4. additiondiluted with water (15 mL)
  5. customThe resulting mixture was separated
  6. extractionthe aqueous phase was extracted with dichloromethane (25 mL*3)
  7. washThe combined organic phase was washed with brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether, 0-25%

Quellen und Nachweise

ORD-Eintrag
ord-6c7a33351cd846989f615d196520051c
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394285B2

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