反应 #710494

反应方程式

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

ammonium acetate

sodium cyanoborohydride

→

desired product

收率 33.2%

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

收率 33.2%

溶剂

methanol

反应条件

后处理

1. 1
   过滤After filtration
2. 2
   浓缩The reaction mixture was concentrated to dryness and 30 mL of ethyl acetate
3. 3
   workup.ADDITIONwere added
4. 4
   洗涤The organic phase was washed with an aqueous solution of 1 N sodium hydroxide, brine and water
5. 5
   干燥dried over magnesium sulfate
6. 6
   过滤filtered
7. 7
   浓缩concentrated to dryness
8. 8
   workup.DISSOLUTIONThe crude material was dissolved in 15 mL of 1 N hydrochloric acid
9. 9
   萃取extracted 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
    萃取was subsequently extracted twice with 15 mL of ethyl acetate
12. 12
    干燥The organic phase was dried over magnesium sulfate
13. 13
    过滤filtered
14. 14
    浓缩concentrated to dryness

实验过程

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.

来源