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

HRID 1890671Notes

Reaction equation

HRID 1890671 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 583357283-(3-Fluorophenyl)morpholine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-b8b30c89ff894e7096ff030295667507
Source dataset
uspto-grants-2013_08
Patent number
US08507488B2

Reaction notes

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