반응 #710494

반응 방정식

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

ammonium acetate

sodium cyanoborohydride

→

desired product

수율 33.2%

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

수율 33.2%

용매

methanol

반응 조건

후처리

1. 1
   여과After filtration
2. 2
   농축The reaction mixture was concentrated to dryness and 30 mL of ethyl acetate
3. 3
   workup.ADDITIONwere added
4. 4
   세척The organic phase was washed with an aqueous solution of 1 N sodium hydroxide, brine and water
5. 5
   건조dried over magnesium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated to dryness
8. 8
   workup.DISSOLUTIONThe crude material was dissolved in 15 mL of 1 N hydrochloric acid
9. 9
   추출extracted 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
    추출was subsequently extracted twice with 15 mL of ethyl acetate
12. 12
    건조The organic phase was dried over magnesium sulfate
13. 13
    여과filtered
14. 14
    농축concentrated to dryness

실험 절차

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.

출처