Réaction #1605797

Équation de réaction

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

methanol

→

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

Rendement 74.3%

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Températurethe reaction mixture was gradually warmed to 0° C
2. 2
   Autreinsoluble matter was removed by filtration
3. 3
   Lavagewashed with tetrahydrofuran
4. 4
   workup.ADDITIONThe filtrate and the washing were mixed
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   workup.ADDITIONTo the residue was added
7. 7
   Autrepurified water (6.3 L)
8. 8
   workup.STIRRINGthe mixture was stirred at room temperature overnight
9. 9
   FiltrationThe precipitate was collected by filtration
10. 10
    Lavagewashed with purified water
11. 11
    LavageFurther, the precipitate was suspension-washed with ethyl acetate (4.8 L)
12. 12
    Filtrationcollected by filtration
13. 13
    Autredried under reduced pressure

Mode opératoire

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)

Source