(2S)-2,5-Dihydro-2-isopropyl-3,6-dimethoxypyrazine → Pyrazine, 2,5-dihydro-3,6-dimethoxy-2-(1-methylethyl)-5-[(2,4,5-trifluorophenyl)methyl]-, (2S,5R)-

HRID 1863918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1863918
[CH3:1][O:2][C:3]1[C@H:4]([CH:11]([CH3:13])[CH3:12])[N:5]=[C:6]([O:9][CH3:10])[CH2:7][N:8]=1.C([Li])CCC.[F:19][C:20]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:21]=1[CH2:22]Br>O1CCCC1>[CH3:1][O:2][C:3]1[C@H:4]([CH:11]([CH3:13])[CH3:12])[N:5]=[C:6]([O:9][CH3:10])[C@@H:7]([CH2:22][C:21]2[CH:24]=[C:25]([F:29])[C:26]([F:28])=[CH:27][C:20]=2[F:19])[N:8]=1

Komponenten

5

Edukt 3

HCID 736065(2S)-2,5-Dihydro-2-isopropyl-3,6-dimethoxypyrazineHCID 27770572,4,5-Trifluorobenzyl BromideHCID 178418339Butyllithium

Produkt 1

HCID 11290377Pyrazine, 2,5-dihydro-3,6-dimethoxy-2-(1-methylethyl)-5-[(2,4,5-trifluorophenyl)methyl]-, (2S,5R)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3.42 g (18.5 mmol) of commercially available (2S)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine in 100 mL of tetrahydrofuran at −70° C. was added 12 mL (19 mmol) of a 1.6M solution of butyllithium in hexanes. After stirring at this temperature for 20 min, 5 g (22.3 mmol) of 2,4,5-trifluorobenzyl bromide in 20 mL of tetrahydrofuran was added and stirring was continued for 3 h before warming the reaction to ambient temperature. The reaction was quenched with water, concentrated in vacuo, and extracted with ethyl acetate. The combined organic phase was washed with brine, dried, and concentrated in vacuo. Purification by flash chromatography (silica gel, 0-5% ethyl acetate in hexanes) afforded the title compound.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 3 h
  3. temperaturebefore warming
  4. customthe reaction to ambient temperature
  5. customThe reaction was quenched with water
  6. concentrationconcentrated in vacuo
  7. extractionextracted with ethyl acetate
  8. washThe combined organic phase was washed with brine
  9. customdried
  10. concentrationconcentrated in vacuo
  11. customPurification by flash chromatography (silica gel, 0-5% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-420b16634b424f8a9ae0eaaf6c5aa07c
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625888B2

Notizen zur Reaktion

Wird geladen…