1,4-Dibromobenzene → (2S)-2-{(S)-[(4-bromophenyl)-(2,4-difluorophenyl)-methyl]-amino}-4-methylpentan-1-ol

HRID 1880538

Reaktionsgleichung

Reaktionsgleichung von HRID 1880538
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[Li]CCCC.[F:14][C:15]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:16]=1[CH:17]=[N:18][CH:19]([CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:20][OH:21]>CCOCC>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C@H:17]([NH:18][C@@H:19]([CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:20][OH:21])[C:16]2[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:15]=2[F:14])=[CH:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 78041,4-DibromobenzeneHCID 574469542-[(2,4-Difluorobenzylidene)-amino]-4-methylpentan-1-olHCID 178418339Butyllithium

Produkt 1

HCID 67298634(2S)-2-{(S)-[(4-bromophenyl)-(2,4-difluorophenyl)-methyl]-amino}-4-methylpentan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a solution of 1,4-dibromobenzene (24.5 g, 100 mmol, 5 eq) in dry ether (200 mL) under nitrogen atmosphere at −30° C., nBuLi (64.75 mL, 1.6 M solution in hexanes, 5 eq) was added and the reaction mixture was stirred for 1 h. A solution of 2-[(2,4-difluorobenzylidene)-amino]-4-methylpentan-1-ol (5 g, 20 mmol) in dry ether was added slowly at −30° C. After stirring for 4 h, the reaction was quenched with water. The ether layer was washed with saturated solution of NaCl, and dried over MgSO4. The solvent was removed under reduced pressure and the crude was flash chromatographed on 500 cm3 of silica gel using 8:2 hexanes:EtOAc as an eluant to yield (2S)-2-{(S)-[(4-bromophenyl)-(2,4-difluorophenyl)-methyl]-amino}-4-methylpentan-1-ol.

Aufarbeitung

  1. stirringAfter stirring for 4 h
  2. customthe reaction was quenched with water
  3. washThe ether layer was washed with saturated solution of NaCl
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customchromatographed on 500 cm3 of silica gel using 8:2 hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d65471211da64ec2986d443ead537f2c
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318748B2

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