Methyl iodide → HCID 58155245, compound

Temperature

-75 °C

A dried flask was charged under an argon atmosphere with a solution of the crude (2S,5R)-5-(3-bromo-phenyl)-4-(4-methoxy-benzyl)-2,5-dimethyl-morpholin-3-one (622 mg) in tetrahydrofuran (16 ml) which was cooled to −75° C. Lithium diisopropylamide (1.54 ml, 3 mmol) was rapidly added, followed by iodomethane (502 mg, 3.5 mmol). After 15 minutes at −75° C. the reaction was complete. For the workup, the cold reaction mixture was quenched with a saturated ammonium chloride solution (15 ml) and extracted with a mixture of dichloromethane (40 ml) and water (15 ml). The organic layer was dried over sodium sulfate and evaporated. The crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate=100/0 to 66/34 as the eluent. The (R)-5-(3-bromo-phenyl)-4-(4-methoxy-benzyl)-2,2,5-trimethyl-morpholin-3-one was obtained as a white solid (495 mg, 77% of theory). Mass (calculated) C21H24BrNO3 [418.334]; (found) [M+H]+=418, [M+2-H]+=420.

1. customFor the workup, the cold reaction mixture
2. customwas quenched with a saturated ammonium chloride solution (15 ml)
3. extractionextracted with a mixture of dichloromethane (40 ml) and water (15 ml)
4. dry with materialThe organic layer was dried over sodium sulfate
5. customevaporated
6. customThe crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate=100/0 to 66/34 as the eluent

ORD record

ord-521a0bdf87c643e6b324c393fd3c0c41

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188079B2