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

Participants

Reaction Steps

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).

Provenance & Evidence