Sodium triacetoxyborohydride → 4-(3-Dimethylamino-propyl)-3-(trifluoromethyl)aniline

In 6 mL of tetrahydrofuran, 100 mg (0.41 mmol) of 3-(4-nitro-2-(trifluoromethyl)phenyl)propionaldehyde was dissolved, and 405 μL (0.81 mmol) of a 2N dimethylamine methanol solution, 171 mg (0.81 mmol) of sodium triacetoxy borohydride and 100 μL of acetic acid were added thereto and the mixture solution was stirred at room temperature overnight. The reaction solution was partitioned between water and ethyl acetate and the organic layer was washed with a saturated sodium chloride solution and concentrated to form an intermediate. This intermediate was dissolved in 10 mL of methanol and stirred on 10 mg of Pd/C (10%) in a hydrogen atmosphere for 20 hours. The catalyst was removed by filtration and the filtrated was concentrated and the obtained residue was purified by a silica gel column (n-hexane:ethyl acetate=5:1) to obtain 109 mg (quantitative) of a target object as a pale yellow oil.

1. customThe reaction solution was partitioned between water and ethyl acetate
2. washthe organic layer was washed with a saturated sodium chloride solution
3. concentrationconcentrated
4. customto form an intermediate
5. customThe catalyst was removed by filtration
6. concentrationthe filtrated was concentrated
7. customthe obtained residue was purified by a silica gel column (n-hexane:ethyl acetate=5:1)
8. customto obtain 109 mg (quantitative) of a target object as a pale yellow oil

ORD record

ord-f81602213eb8428d8eb0bde9afd0c6ef

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609656B2