Reaktion #90307

Reaktionsgleichung

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

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeResulting
2. 2
   Sonstigereaction mixture
3. 3
   Sonstigeresulting suspension
4. 4
   workup.STIRRINGwas then stirred for 4-5 hrs
5. 5
   SonstigeReaction
6. 6
   Sonstigewas then quenched with methanol
7. 7
   Einengenconcentrated to dryness
8. 8
   SonstigeReaction mixture
9. 9
   Extraktionsodium hydroxide solution and extracted with chloroform
10. 10
    TrocknenOrganic layer was dried over sodium sulphate
11. 11
    Einengenconcentrated under reduced pressure
12. 12
    Sonstigeto yield sticky solid
13. 13
    SonstigeProduct was then purified by silica gel column chromatography

Vorschrift

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.

Quelle