Sodium bis(2-methoxyethoxy)aluminiumhydride → (3R)-4-Benzyl-3-methylmorpholine

Participants

Reaction Conditions

Reaction Steps

To a solution of (5R)-5-methyl-4-(phenylmethyl)-3-morpholinone (11.7 g, 57 mmol) in toluene (140 mL) at 0° C. was added sodium bis(2-methoxyethoxy)aluminumhydride (Red-Al) (35 mL, 3 mL/g of morpholinone) slowly via addition funnel, and the reaction mixture was stirred overnight at 60° C. The reaction was cooled down to 0° C. and quenched by dropwise addition of 1N aqueous NaOH (15 mL). The resulting mixture was partitioned between Et2O (100 mL) and of 1N aqueous NaOH (100 mL). The organic layer was separated, and the aqueous layer was further extracted with Et2O (50 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated. The resulting residue was azeotroped with CH3OH (50 mL) to afford the title compound (10.69 g) as a colorless oil. LC-MS (ES) m/z=192 [M+H]+

Provenance & Evidence