Hydrochloric Acid → (s)-2-(3,4-Dichlorophenyl)morpholine

Participants

Reaction Conditions

Reaction Steps

Synthesized according to General Procedure 35. To a stirring solution of (R)-1-((S)-2-(3,4-dichlorophenyl)-morpholino)-2-methoxy-2-phenylethanone (620 mg, 1.63 mmol) and THF (9 mL), under N2, at 0° C., was added a solution of Super-hydride in THF (1.0 M, 10.3 mL, 10.3 mmol) dropwise over 10 minutes. The solution was stirred at 0° C. for 30 minutes. The solution was poured into 1M aqueous HCl solution (20 mL). The solution was then basified with NH4OH and extracted with CH2Cl2 (3×50 mL). Purified via silica gel chromatography using 10% MeOH in CH2Cl2 to obtain the desired morpholine, arbitrarily assigned the (5) configuration, as a clear oil (250 mg, 1.1 mmol, 67% yield). 1H-NMR (400 MHz, CDCl3) δ 7.50-7.49 (m, 2H), 7.19 (dd, J=1.6, 8.3 Hz, 1H), 4.47 (dd, J=2.4, 10.4 Hz, 1H), 4.09 (s, 1H), 4.08 (dd, J=1.9, 12.9 Hz, 1H), 3.82-3.75 (m, 1H), 3.09 (dd, J=2.5, 12.5 Hz, 1H), 2.97 (dd, J=3.1, 10.2 Hz, 2H), 2.72-2.69 (m, 1H). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=232.3; tR=0.65 min.

Provenance & Evidence