تفاعل #1605797

معادلة التفاعل

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

methanol

→

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

المردود 74.3%

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture was gradually warmed to 0° C
2. 2
   أخرىinsoluble matter was removed by filtration
3. 3
   غسيلwashed with tetrahydrofuran
4. 4
   workup.ADDITIONThe filtrate and the washing were mixed
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   workup.ADDITIONTo the residue was added
7. 7
   أخرىpurified water (6.3 L)
8. 8
   workup.STIRRINGthe mixture was stirred at room temperature overnight
9. 9
   ترشيحThe precipitate was collected by filtration
10. 10
    غسيلwashed with purified water
11. 11
    غسيلFurther, the precipitate was suspension-washed with ethyl acetate (4.8 L)
12. 12
    ترشيحcollected by filtration
13. 13
    أخرىdried under reduced pressure

الإجراء التجريبي

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)

المصدر