반응 #90307

반응 방정식

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

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타Resulting
2. 2
   기타reaction mixture
3. 3
   기타resulting suspension
4. 4
   workup.STIRRINGwas then stirred for 4-5 hrs
5. 5
   기타Reaction
6. 6
   기타was then quenched with methanol
7. 7
   농축concentrated to dryness
8. 8
   기타Reaction mixture
9. 9
   추출sodium hydroxide solution and extracted with chloroform
10. 10
    건조Organic layer was dried over sodium sulphate
11. 11
    농축concentrated under reduced pressure
12. 12
    기타to yield sticky solid
13. 13
    기타Product was then purified by silica gel column chromatography

실험 절차

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.

출처