4-Methyl-3-nitro-1,1,1-trifluoro-2-pentanol → 3-Amino-1,1,1-trifluoro-4-methylpentan-2-ol

Temperature

5 °C

A solution of 4-methyl-3-nitro-1,1,1-trifluoro-2-pentanol (17.1 g) in isopropanol (115 ml) and acetic acid (0.43 ml) was hydrogenated over 10% palladium on carbon (2.4 g) at 3.5 bar pressure until uptake of hydrogen was complete. The catalyst was removed by filtration through diatomaceous earth and the filter cake washed with isopropanol. The filtrate was evaporated under vacuum until no further isopropanol distilled and the residue dissolved in acetonitrile (40 ml). A solution of oxalic acid (3.94 g) in acetonitrile (80 ml) was added with stirring and the mixture cooled to 5° C. The product which crystallised was collected by filtration, washed with cold acetonitrile and dried at 50° C. to give 3-amino-4-methyl-1,1,1-trifluoro-2-pentanol as its oxalate salt (9.08 g).

1. customThe catalyst was removed by filtration through diatomaceous earth
2. washthe filter cake washed with isopropanol
3. customThe filtrate was evaporated under vacuum until no further isopropanol
4. distillationdistilled
5. dissolutionthe residue dissolved in acetonitrile (40 ml)
6. additionA solution of oxalic acid (3.94 g) in acetonitrile (80 ml) was added
7. customThe product which crystallised
8. filtrationwas collected by filtration
9. washwashed with cold acetonitrile
10. customdried at 50° C.

ORD record

ord-3d09f83bd90f4cb3990d7f13257d5ac3

Source dataset

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06054593