Reacción #1605823

Ecuación de reacción

5-(2-bromoacetyl)-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one

methanol

→

5-[(1R)-2-bromo-1-hydroxyethyl]-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one

Rendimiento 42.5%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was warmed gradually to 0° C
2. 2
   Filtracióninsoluble matter was filtered off
3. 3
   Lavadowashed with tetrahydrofuran
4. 4
   workup.ADDITIONThe filtrate and the washing were mixed
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   workup.ADDITIONTo the residue was added
7. 7
   Otropurified water (100 mL)
8. 8
   workup.STIRRINGthe mixture was stirred at room temperature overnight
9. 9
   FiltraciónThe precipitate was collected by filtration
10. 10
    Lavadowashed with purified water
11. 11
    LavadoThe precipitate was further suspension-washed with ethyl acetate (200 mL)
12. 12
    Filtracióncollected by filtration
13. 13
    Otrodried under reduced pressure

Procedimiento

Under an argon flow, 5-(2-bromoacetyl)-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one (7.15 g, 17.8 mmol) was suspended in dehydrated tetrahydrofuran (40 mL), the CBS catalyst (493 mg) was added thereto, and the reaction mixture was stirred at −20° C. for 40 minutes. After adding dropwise a 1.0 M solution of borane-tetrahydrofuran complex in tetrahydrofuran (21.4 mL) at the same temperature, the mixture was warmed gradually to 0° C. After adding methanol (20 mL) dropwise, insoluble matter was filtered off and washed with tetrahydrofuran. The filtrate and the washing were mixed and concentrated under reduced pressure. To the residue was added purified water (100 mL) and the mixture was stirred at room temperature overnight. The precipitate was collected by filtration and washed with purified water. The precipitate was further suspension-washed with ethyl acetate (200 mL), collected by filtration, and dried under reduced pressure to obtain 5-[(1R)-2-bromo-1-hydroxyethyl]-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one (3.06 g).

Fuente