Hydroxylamine → 4,4,5,5,5-Pentafluoro-1-(pyridin-2-yl)pentan-1-amine

Temperature

25 °C

Hydroxylamine (0.216 mL, 3.53 mmol) was added to a solution of 4,4,5,5,5-pentafluoro-1-(pyridin-2-yl)pentan-1-one (0.894 g, 3.53 mmol) in MeOH (10.87 mL) and the resulting solution was stirred at 25° C. for 5 h. Another 1 eq. hydroxylamine was added and the reaction was stirred overnight. Another 2 eq hydroxylamine was added and the reaction was stirred overnight. The reaction mixture was concentrated in vacuo and the resulting residue was diluted with EtOAc and the resulting organic phase was washed with water and brine, then dried (Na2SO4) and concentrated in vacuo to give the crude oxime, as a colorless solid. This was redissolved in TFA (6.52 mL) and cooled to 0° C. Zinc (1.155 g, 17.66 mmol) was added in one portion. After 3 h at 0° C. the reaction mixture was poured into a mixture of ice and 5 N aq. NaOH. The pH was adjusted to pH 10. The mixture was extracted with DCM (3×). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give the desired amine product. m/z=255.1 (M+H).

1. stirringthe reaction was stirred overnight
2. stirringthe reaction was stirred overnight
3. concentrationThe reaction mixture was concentrated in vacuo
4. additionthe resulting residue was diluted with EtOAc
5. washthe resulting organic phase was washed with water and brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customto give the crude oxime
9. temperaturecooled to 0° C
10. extractionThe mixture was extracted with DCM (3×)
11. dry with materialThe combined organic extracts were dried (Na2SO4)
12. concentrationconcentrated in vacuo

ORD record

ord-0a4d34e91aa34624af6457637492f7d2

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365574B2