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

HRID 2223554

反応式

HRID 2223554 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

To a solution of 1,4-dibromobenzene (24.5 g, 100 mmol, 5eq) 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.

後処理

  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

出典と根拠

ORDレコード
ord-5644f3a3421a4858b45e1b1a9c65db0c
出典データセット
uspto-grants-2008_05
特許番号
US07375134B2

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