Aluminium lithium hydride → 3-(3-Fluorophenyl)morpholine

HRID 1890671ノート

反応式

HRID 1890671 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[NH:13][C:12](=O)[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:9][O:10][CH2:11][CH2:12][NH:13]2)[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 583357985-(3-Fluorophenyl)morpholin-3-one

生成物 1

HCID 583357283-(3-Fluorophenyl)morpholine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In step 2-4, a solution of 5-(3-fluorophenyl)morpholin-3-one (4.56 g, 23.4 mmol) in THF at 0° C. was treated with lithium aluminum hydride (4.3 g, 107 mmol) in a single portion. The suspension was warmed to room temperature and stirred overnight. The reaction mixture was quenched with Na2SO4 10 H2O and stirred for 4 hours. The heterogeneous solution was filtered through a celite pad, and the filtrate was concentrated and purified with flash chromatography (5-10% methanol/EtOAc) to obtain 3-(3-fluorophenyl)morpholine (2-4) as a clear oil. 1H NMR CDCl3 (δ) ppm 7.28 (m, 1H), 7.13 (m, 2H), 6.97 (m, 1H), 3.93 (dd, 1H), 3.89 (m, 1H), 3.81 (dd, 1H), 3.64 (td, 1H), 3.35 (m, 1H), 3.12 (td, 1H), 3.02 (m, 1H).

後処理

  1. customThe reaction mixture was quenched with Na2SO4 10 H2O
  2. stirringstirred for 4 hours
  3. filtrationThe heterogeneous solution was filtered through a celite pad
  4. concentrationthe filtrate was concentrated
  5. custompurified with flash chromatography (5-10% methanol/EtOAc)

出典と根拠

ORDレコード
ord-b8b30c89ff894e7096ff030295667507
出典データセット
uspto-grants-2013_08
特許番号
US08507488B2

反応ノート

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