2,4,4,6-Tetrabromocyclohexa-2,5-dienone → methyl (2S)-1-(6-bromo-1,3-benzoxazol-2-yl)-2-piperidinecarboxylate

HRID 412656

Reaktionsgleichung

Reaktionsgleichung von HRID 412656
Br[C:2]1[C:3](=O)[C:4](Br)=[CH:5][C:6]([Br:9])(Br)[CH:7]=1.[O:12]1C2C=CC=CC=2[N:14]=[C:13]1[N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]1[C:27]([O:29][CH3:30])=[O:28]>ClCCl>[Br:9][C:6]1[CH:7]=[CH:2][C:3]2[N:14]=[C:13]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]3[C:27]([O:29][CH3:30])=[O:28])[O:12][C:4]=2[CH:5]=1

Komponenten

4

Edukt 2

HCID 884332,4,4,6-Tetrabromocyclohexa-2,5-dienoneHCID 10220819methyl (2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylate

Produkt 1

HCID 9949771methyl (2S)-1-(6-bromo-1,3-benzoxazol-2-yl)-2-piperidinecarboxylateAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one (4.7 g) was added to a solution of methyl (2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxylate (3.0 g) [see Preparation 2] in dichloromethane (60 ml) at −10° C. over a period of 10 minutes. The reaction mixture was then warmed to room temperature and diluted with dichloromethane. The organic layer was washed with saturated sodium hydrogen carbonate, then with 1N sodium hydroxide solution, dried over sodium sulphate and the solvent removed under reduced pressure to afford methyl (2S)-1-(6-bromo-1,3-benzoxazol-2-yl)-2-piperidinecarboxylate (3.7 g) as a purple coloured oil.

Aufarbeitung

  1. washThe organic layer was washed with saturated sodium hydrogen carbonate
  2. dry with materialwith 1N sodium hydroxide solution, dried over sodium sulphate
  3. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d28894faf6d1432a999cc21be042e341
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562964B1

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