Réaction #90307

Équation de réaction

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

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   AutreResulting
2. 2
   Autrereaction mixture
3. 3
   Autreresulting suspension
4. 4
   workup.STIRRINGwas then stirred for 4-5 hrs
5. 5
   AutreReaction
6. 6
   Autrewas then quenched with methanol
7. 7
   Concentrationconcentrated to dryness
8. 8
   AutreReaction mixture
9. 9
   Extractionsodium hydroxide solution and extracted with chloroform
10. 10
    SéchageOrganic layer was dried over sodium sulphate
11. 11
    Concentrationconcentrated under reduced pressure
12. 12
    Autreto yield sticky solid
13. 13
    AutreProduct was then purified by silica gel column chromatography

Mode opératoire

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.

Source