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

HRID 131184

반응식

HRID 131184 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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])

출처 및 근거

ORD 기록
ord-a1606e5abd05412897a62fe2d03a68d4
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384941B2

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