反応 #1605797

反応方程式

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

methanol

→

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

収率 74.3%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   温度the reaction mixture was gradually warmed to 0° C
2. 2
   その他insoluble matter was removed by filtration
3. 3
   洗浄washed with tetrahydrofuran
4. 4
   workup.ADDITIONThe filtrate and the washing were mixed
5. 5
   濃縮concentrated under reduced pressure
6. 6
   workup.ADDITIONTo the residue was added
7. 7
   その他purified water (6.3 L)
8. 8
   workup.STIRRINGthe mixture was stirred at room temperature overnight
9. 9
   ろ過The precipitate was collected by filtration
10. 10
    洗浄washed with purified water
11. 11
    洗浄Further, the precipitate was suspension-washed with ethyl acetate (4.8 L)
12. 12
    ろ過collected by filtration
13. 13
    その他dried under reduced pressure

実験手順

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)

出典