Phenylalanine amide → (2S)-3-Phenylpropane-1,2-diamine

Temperature

0 °C

To a stirred solution of (S)-2-amino-3-phenylpropanamide (2.92 g, 17.78 mmol) in tetrahydrofuran (50 mL) at 0° C. under nitrogen atmosphere was dropwise added lithium aluminum hydride (18.0 mL of 2.0 M solution in tetrahydrofuran, 36.0 mmol). The resulting reaction mixture was stirred at reflux for 2 h, and then cooled to 0° C. and quenched with sodium sulfate decahydrate. The resulting precipitate was filtered, and the filter cake was washed with ethyl acetate (250 mL). The filtrate was concentrated in vacuo to afford (S)-3-phenylpropane-1,2-diamine as yellowish oil in 97% yield (2.60 g): 1H NMR (300 MHz, CDCl3) δ 7.35-7.17 (m, 5H), 3.02-2.92 (m, 1H), 2.85-2.74 (m, 2H), 2.60-2.45 (m, 2H), 1.47 (br s, 4H).

1. customat 0° C.
2. customThe resulting reaction mixture
3. temperatureat reflux for 2 h
4. customquenched with sodium sulfate decahydrate
5. filtrationThe resulting precipitate was filtered
6. washthe filter cake was washed with ethyl acetate (250 mL)
7. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-6291d748c5a844c7a975beb5c0d5c161

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293768B2