Реакция #90307

Уравнение реакции

Sodium triacetoxyborohydride

acetic acid

tetrahydro-pyran-4-one

4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl) butan-1-amine

→

N-[4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]tetrahydro-2H-pyran-4-amine

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   ДругоеResulting
2. 2
   Другоеreaction mixture
3. 3
   Другоеresulting suspension
4. 4
   workup.STIRRINGwas then stirred for 4-5 hrs
5. 5
   ДругоеReaction
6. 6
   Другоеwas then quenched with methanol
7. 7
   Концентрированиеconcentrated to dryness
8. 8
   ДругоеReaction mixture
9. 9
   Экстракцияsodium hydroxide solution and extracted with chloroform
10. 10
    СушкаOrganic layer was dried over sodium sulphate
11. 11
    Концентрированиеconcentrated under reduced pressure
12. 12
    Другоеto yield sticky solid
13. 13
    ДругоеProduct was then purified by silica gel column chromatography

Методика

To a suspension of 4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl) butan-1-amine obtained in step VI of example I in tetrahydrofuran was added acetic acid (1 eq.) and tetrahydro-pyran-4-one (1.1 eq.). Resulting reaction mixture was stirred for 10 min. Sodium triacetoxyborohydride (2.2 eq.) was added to reaction mixture over a period of 1 hrs and resulting suspension was then stirred for 4-5 hrs. Reaction was then quenched with methanol and concentrated to dryness. Reaction mixture was basified using aq.sodium hydroxide solution and extracted with chloroform. Organic layer was dried over sodium sulphate and concentrated under reduced pressure to yield sticky solid. Product was then purified by silica gel column chromatography to afford N-[4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]tetrahydro-2H-pyran-4-amine.

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