반응 #1605797

반응 방정식

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

methanol

→

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

수율 74.3%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   온도the reaction mixture was gradually warmed to 0° C
2. 2
   기타insoluble matter was removed by filtration
3. 3
   세척washed with tetrahydrofuran
4. 4
   workup.ADDITIONThe filtrate and the washing were mixed
5. 5
   농축concentrated under reduced pressure
6. 6
   workup.ADDITIONTo the residue was added
7. 7
   기타purified water (6.3 L)
8. 8
   workup.STIRRINGthe mixture was stirred at room temperature overnight
9. 9
   여과The precipitate was collected by filtration
10. 10
    세척washed with purified water
11. 11
    세척Further, the precipitate was suspension-washed with ethyl acetate (4.8 L)
12. 12
    여과collected by filtration
13. 13
    기타dried under reduced pressure

실험 절차

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)

출처