4-Methoxybenzyl bromide → HCID 58155181, compound

Temperature

0 °C

A solution of (R)-5-(3-amino-phenyl)-4-(4-methoxy-benzyl)-5-methyl-morpholin-3-one (1.0 g, 3.7 mmol) in N,N-dimethylformamide was added within 5 minutes at 0° C. to a solution of potassium tert-butanolate (0.636 g, 5.7 mmol). After stirring at 0° C. for 30 minutes the light yellow solution was cooled to −4° C. and treated with a solution of 4-methoxybenzylbromide (1.12 g, 5.6 mmol) in N,N-dimethylformamide (4 ml). The reaction mixture was left to warm to room temperature, then the solvent was evaporated at reduced pressure, and the residue treated with saturated ammonium chloride solution (50 ml) and ethyl acetate (100 ml). The organic layer was separated, washed with brine (50 ml), dried over sodium sulfate, and evaporated at reduced pressure. The crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate=100/0 to 50/50 as the eluent. The (R)-5-(3-bromo-phenyl)-4-(4-methoxy-benzyl)-5-methyl-morpholin-3-one was obtained as colorless oil (1.19 g, 83% of theory). Mass (calculated) C19H20BrNO3 [390.275]; (found) [M+H]+=390, [M+2-H]+=392.

1. temperaturewas cooled to −4° C.
2. waitThe reaction mixture was left
3. temperatureto warm to room temperature
4. customthe solvent was evaporated at reduced pressure
5. additionthe residue treated with saturated ammonium chloride solution (50 ml) and ethyl acetate (100 ml)
6. customThe organic layer was separated
7. washwashed with brine (50 ml)
8. dry with materialdried over sodium sulfate
9. customevaporated at reduced pressure
10. customThe crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate=100/0 to 50/50 as the eluent

ORD record

ord-df916bd456fe46e29356ad28103a1908

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188079B2