Реакция #1605823

Уравнение реакции

5-(2-bromoacetyl)-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one

methanol

→

5-[(1R)-2-bromo-1-hydroxyethyl]-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one

Выход 42.5%

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Температураthe mixture was warmed gradually to 0° C
2. 2
   Фильтрацияinsoluble matter was filtered off
3. 3
   Промывкаwashed with tetrahydrofuran
4. 4
   workup.ADDITIONThe filtrate and the washing were mixed
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   workup.ADDITIONTo the residue was added
7. 7
   Другоеpurified water (100 mL)
8. 8
   workup.STIRRINGthe mixture was stirred at room temperature overnight
9. 9
   ФильтрацияThe precipitate was collected by filtration
10. 10
    Промывкаwashed with purified water
11. 11
    ПромывкаThe precipitate was further suspension-washed with ethyl acetate (200 mL)
12. 12
    Фильтрацияcollected by filtration
13. 13
    Другоеdried under reduced pressure

Методика

Under an argon flow, 5-(2-bromoacetyl)-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one (7.15 g, 17.8 mmol) was suspended in dehydrated tetrahydrofuran (40 mL), the CBS catalyst (493 mg) was added thereto, and the reaction mixture was stirred at −20° C. for 40 minutes. After adding dropwise a 1.0 M solution of borane-tetrahydrofuran complex in tetrahydrofuran (21.4 mL) at the same temperature, the mixture was warmed gradually to 0° C. After adding methanol (20 mL) dropwise, insoluble matter was filtered off and washed with tetrahydrofuran. The filtrate and the washing were mixed and concentrated under reduced pressure. To the residue was added purified water (100 mL) and the mixture was stirred at room temperature overnight. The precipitate was collected by filtration and washed with purified water. The precipitate was further suspension-washed with ethyl acetate (200 mL), collected by filtration, and dried under reduced pressure to obtain 5-[(1R)-2-bromo-1-hydroxyethyl]-8-[(4-methoxyphenyl)methoxy]-1,2-dihydroquinolin-2-one (3.06 g).

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