3-Morpholinone → HCID 59167001, compound

Participants

Reaction Conditions

Reaction Steps

(S)-2-[(S)-Phenyl-(pyridin-3-yloxy)-methyl]-morpholine was synthesized from the corresponding amide (6-[Phenyl-(pyridin-3-yloxy)-methyl]-morpholin-3-one) (see Scheme G, compound 8) using the following procedure: A solution of compound 1 (0.30 g, 0.85 mmol) in anhydrous toluene (3.0 mL) was placed under a nitrogen atmosphere, cooled to 0° C. and a commercial solution of Red-Al (65 wt % in toluene, 1.0 mL, 3.3 mmol) was added dropwise via syringe. The reaction mixture was warmed to room temperature over 4 h. TLC analysis showed no starting material remaining. The reaction mixture was again cooled to 0° C. and quenched by the dropwise addition of 2N sodium hydroxide. The reaction mixture was diluted with toluene, the aqueous phase separated and further extracted with toluene. The combined organic extracts were dried over sodium sulphate, filtered, and solvent was removed under reduced pressure to give 0.30 g of light brown oil. Two chromatographies of the reaction product on silica gel (eluent—3:1 ethyl acetate/methanol the second) gave 0.080 g (35%) of the desired product. 1H NMR (400 MHz, CDCl3) δ 8.32 (m, 1H), 8.12 (m, 1H), 7.24 (m, 5H), 7.10 (m, 2H), 5.10 (d, 1H), 3.96 (m, 2H), 3.68 (m, 1H), 2.84 (m, 2H), 2.66 (m, 2H), 1.84 (br s, 1H). (MS) m/z 271.05 [C16H18N2O2+H+]; CHN—C16H18N2O2 Calc'd: C, 71.09%; H, 6.71%; N, 10.36%. Found: C, 70.49%; H, 6.70%; N, 9.83%.

Provenance & Evidence