Triphenylphosphane dibromide → (2S)-4-Benzyl-2-[bromo(phenyl)methyl]morpholine

HRID 131184ノート

反応式

HRID 131184 の反応式
[C:1]1([C@@H:7]([C@H:9]2[O:14][CH2:13][CH2:12][N:11]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10]2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-:22].[Br-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)Cl>[Br:22][C@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C@H:9]1[O:14][CH2:13][CH2:12][N:11]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10]1

参加物

4

反応物 2

HCID 12890784Triphenylphosphane dibromideHCID 58997981(S)-Phenyl[(2S)-4-(phenylmethyl)morpholin-2-yl]methanol

生成物 1

HCID 58997979(2S)-4-Benzyl-2-[bromo(phenyl)methyl]morpholine収率 81%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
60 °C

実験手順

To a solution of 4a (4.71 g, 16.6 mmol) in anhydrous chloroform (200 ml) under nitrogen was added triphenylphosphine dibromide (14.04 g, 33.26 mmol). The reaction mixture was heated at 60° C. overnight. The mixture was allowed to cool to room temperature then washed with saturated aqueous sodium carbonate solution, dried over sodium sulphate and concentrated in vacuo. The resulting residue was purified by flash chromatography on silica (eluent: ethyl acetate/isohexane gradient 10/90 to 30/70 [v/v]) to give 5a as a white solid (4.63 g, 81%); MW 346.27; C18H20BrNO; 1H NMR (CDCl3): 7.14-7.39 (10H, m), 4.83 (1H, d, 7 Hz), 4.01 (1H, br, t, 8 Hz), 3.73 (1H, br, d, 11 Hz), 3.60-3.48 (2H, m), 3.39 (1H, d, 12 Hz), 3.20 (1H, d, 11 Hz), 2.50 (1H, d, 10 Hz), 2.07 (2H, t, 10 Hz); LCMS: (6 min method) m/z 346 [M]+ @ Rt 2.51 min.

後処理

  1. temperatureto cool to room temperature
  2. washthen washed with saturated aqueous sodium carbonate solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by flash chromatography on silica (eluent: ethyl acetate/isohexane gradient 10/90 to 30/70 [v/v])

出典と根拠

ORDレコード
ord-a1606e5abd05412897a62fe2d03a68d4
出典データセット
uspto-grants-2008_06
特許番号
US07384941B2

反応ノート

読み込み中…