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

HRID 1890671노트

반응식

HRID 1890671 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 583357283-(3-Fluorophenyl)morpholine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b8b30c89ff894e7096ff030295667507
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507488B2

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