Imidazole → (R)-4-(3-Iodo-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

HRID 1191514ノート

反応式

HRID 1191514 の反応式
O[CH2:2][C@H:3]([CH3:16])[CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:41]I>C(Cl)Cl>[I:41][CH2:2][C@H:3]([CH3:16])[CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:15]

参加物

6

反応物 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 68910321(R)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one

生成物 1

HCID 68908541(R)-4-(3-Iodo-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one収率 87.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A reaction flask was charged with (R)-4-(3-Hydroxy-2-methylpropyl]-4H-benzo[1,4]oxazin-3-one (1.71 g, 7.77 mmol), triphenylphosphine (4.50 g, 17.2 mmol), imidazole (1.27, 18.7 mmol), and iodine (5.54 g, 21.8 mmol) in CH2Cl2 (20 mL) and stirred at rt for 20 h. The reaction mixture was washed with saturated sodium thiosulfate, dried over Na2SO4, filtered, and concentrated. The product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 2:1) to give the title compound (2.25 g, 87%).

後処理

  1. washThe reaction mixture was washed with saturated sodium thiosulfate
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by flash column chromatography (SiO2; n-heptane/EtOAc 2:1)

出典と根拠

ORDレコード
ord-dbe9e68a9f6141b695176bbdf8f88477
出典データセット
uspto-grants-2014_03
特許番号
US08680115B2

反応ノート

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