Phenylalanine amide → (2S)-3-Phenylpropane-1,2-diamine
Reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([NH2:5])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:7]1([CH2:6][C@H:2]([NH2:1])[CH2:3][NH2:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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 (in, 1H), 2.85-2.74 (m, 2H), 2.60-2.45 (m, 2H), 1.47 (br s, 4H).
Workup
- customat 0° C.
- customThe resulting reaction mixture
- temperatureat reflux for 2 h
- customquenched with sodium sulfate decahydrate
- filtrationThe resulting precipitate was filtered
- washthe filter cake was washed with ethyl acetate (250 mL)
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-af60fd3660fb4e0dac972f580d09bd32
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063084B2
Reaction notes
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