Reacción #1605797

Ecuación de reacción

8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one

methanol

→

8-benzyloxy-5-((R)-2-bromo-1-hyroxyethyl)-1H-quinolin-2-one

Rendimiento 74.3%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture was gradually warmed to 0° C
2. 2
   Otroinsoluble matter was removed by filtration
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 (6.3 L)
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
    LavadoFurther, the precipitate was suspension-washed with ethyl acetate (4.8 L)
12. 12
    Filtracióncollected by filtration
13. 13
    Otrodried under reduced pressure

Procedimiento

Under an argon flow, 8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one (374 g, 1.00 mol) was suspended in dehydrated tetrahydrofuran (3.8 L), CBS catalyst (27.8 g) was added thereto, and the mixture was stirred at −55 to −45° C. for 40 minutes. After adding dropwise a 0.9 M tetrahydrofuran solution of borane-tetrahydrofuran complex (1.27 L) at the same temperature, the reaction mixture was gradually warmed to 0° C. After adding methanol (1.3 L) dropwise, insoluble matter was removed by filtration and washed with tetrahydrofuran. The filtrate and the washing were mixed and concentrated under reduced pressure. To the residue was added purified water (6.3 L), and the mixture was stirred at room temperature overnight. The precipitate was collected by filtration and washed with purified water. Further, the precipitate was suspension-washed with ethyl acetate (4.8 L), collected by filtration, and dried under reduced pressure to obtain 8-benzyloxy-5-((R)-2-bromo-1-hyroxyethyl)-1H-quinolin-2-one (278 g). 1H-NMR (400 MHz, CDCl3) δ 9.26 (s, 1H), 8.08 (d, J=10.0 Hz, 1H), 7.37-7.45 (m, 5H), 7.28 (d, J=8.0 Hz, 1H), 7.05 (d, J=8.0 Hz, 1H), 6.72 (d, J=10.0 Hz, 1H), 5.33 (dd, J=9.0 Hz, 4.0 Hz, 1H), 5.19 (s, 2H), 3.71-3.74 (m, 2H)

Fuente