Acetic Acid → HCID 13499164, compound

After briskly stirring a mixture of 1,1,1-trifluoroacetone (1.0 ml; 11.2 mmol), benzylamine (1.1 ml; 10 mmol), AcOH (2 ml) and 3 Å molecular sieves (5 g) in 30 ml of CH2Cl2 for 2 hour at room temperature, sodium triacetoxyborohydride (4.25 g; 20 mmol) was added. After stirring 48 hours at room temperature, the reaction mixture was filtered through celite. After removing the volatiles in vacuo the residue was partitioned between ether (100 ml) and 1N NaOH (100 ml). The organic layer was washed with brine (50 ml), dried (MgSO4) and filtered through a 5×5 cm pad of silica gel. The pad was rinsed with ether and the filtrate was concentrated to afford 2.0 g (99%) of the title compound of this step as a colorless liquid.

1. stirringAfter stirring 48 hours at room temperature
2. filtrationthe reaction mixture was filtered through celite
3. customAfter removing the volatiles in vacuo the residue
4. customwas partitioned between ether (100 ml) and 1N NaOH (100 ml)
5. washThe organic layer was washed with brine (50 ml)
6. dry with materialdried (MgSO4)
7. filtrationfiltered through a 5×5 cm pad of silica gel
8. washThe pad was rinsed with ether
9. concentrationthe filtrate was concentrated

ORD record

ord-a097edd5a1564f2aa33dcbdcbe164778

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05846990