Methanesulfonic Acid → (2S)-3,3,3-Trifluoro-2-methylpropane-1,2-diamine

A mixture of 10.50 g (70 mmol) of (R)-2-((S)-1-aminomethyl-2,2,2-trifluoro-1-methylethylamino)-2-phenylethanol in methanol, 4.5 mL (68 mmol) of methanesulfonic acid and 1.50 g of Pd(OH)2/C (20% w/w) is hydrogenated at 25° C. in an autoclave, under a hydrogen pressure of 5 bar, for 24 hours. The mixture obtained is then filtered and the filtrate is evaporated to dryness. The oil obtained is taken up in 3 M hydrochloric acid solution (42 mL). The mixture obtained is extracted with ethyl ether. Ethyl ether and 15 mL of 35% sodium hydroxide are then added to the aqueous phase, to pH 12. The aqueous phase is then separated out by settling and extracted with 3 times 200 mL of ethyl ether. The organic phases are combined, dried over magnesium sulfate, filtered and then concentrated under vacuum to give 4.50 g of (S)-3,3,3-trifluoro-2-methylpropane-1,2-diamine in the form of a pale yellow oil, the characteristics of which are as follows:

1. customis hydrogenated at 25° C. in an autoclave, under a hydrogen
2. customThe mixture obtained
3. filtrationis then filtered
4. customthe filtrate is evaporated to dryness
5. customThe oil obtained
6. customThe mixture obtained
7. extractionis extracted with ethyl ether
8. additionEthyl ether and 15 mL of 35% sodium hydroxide are then added to the aqueous phase, to pH 12
9. customThe aqueous phase is then separated out
10. extractionextracted with 3 times 200 mL of ethyl ether
11. dry with materialdried over magnesium sulfate
12. filtrationfiltered
13. concentrationconcentrated under vacuum

ORD record

ord-69df3f68c9354aeea8534feb59977f3c

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321790B2