Reaktion #710494

Reaktionsgleichung

1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-one

ammonium acetate

sodium cyanoborohydride

→

desired product

Ausbeute 33.2%

3-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-amine

Ausbeute 33.2%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationAfter filtration
2. 2
   EinengenThe reaction mixture was concentrated to dryness and 30 mL of ethyl acetate
3. 3
   workup.ADDITIONwere added
4. 4
   WaschenThe organic phase was washed with an aqueous solution of 1 N sodium hydroxide, brine and water
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated to dryness
8. 8
   workup.DISSOLUTIONThe crude material was dissolved in 15 mL of 1 N hydrochloric acid
9. 9
   Extraktionextracted with 15 mL of ethyl acetate
10. 10
    workup.ADDITIONAn aqueous solution of 1 N sodium hydroxide was added to the aqueous phase, which
11. 11
    Extraktionwas subsequently extracted twice with 15 mL of ethyl acetate
12. 12
    TrocknenThe organic phase was dried over magnesium sulfate
13. 13
    Filtrationfiltered
14. 14
    Einengenconcentrated to dryness

Vorschrift

0.64 g of 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-one (Int-12) (0.0025 mol) were diluted in 5 mL of methanol. 7.0 g of molecular sieves 3 Å, 1.90 g (0.025 mol) of ammonium acetate and 0.39 g (0.0052 mol) of sodium cyanoborohydride were added. The reaction medium was stirred overnight at room temperature. After filtration, the pH was adjusted to 9 with an aqueous solution of 1 N sodium hydroxide. The reaction mixture was concentrated to dryness and 30 mL of ethyl acetate were added. The organic phase was washed with an aqueous solution of 1 N sodium hydroxide, brine and water; dried over magnesium sulfate, filtered and concentrated to dryness. The crude material was dissolved in 15 mL of 1 N hydrochloric acid and extracted with 15 mL of ethyl acetate. An aqueous solution of 1 N sodium hydroxide was added to the aqueous phase, which was subsequently extracted twice with 15 mL of ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated to dryness. 0.21 g (32%) of desired product 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-amine (IIa-16) were obtained, [M+1]=253.

Quelle