Butanal → Methyl 3-(4-(butylamino)phenyl)propanoate
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH:14](=O)[CH2:15][CH2:16][CH3:17]>>[CH2:14]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1)[CH2:15][CH2:16][CH3:17]Participants
3
Procedure
Following a procedure analogous to that for the synthesis Example 106, methyl 3-(4-aminophenyl)propanoate (Jakobsen, C. M. et al., J. Med. Chem., 44:4696-4703 (2001)) (896 mg, 5.00 mmol) and butyraldehyde (397 mg, 5.50 mmol) were converted to the title compound (420 mg, 44%). 1H NMR (CDCl3) δ 7.01 (d, J=8.4 Hz, 2H), 6.60-6.47 (m, 2H), 3.68 (s, 3H), 3.10 (t, J=7.2 Hz, 2H), 2.89-2.77 (m, 2H), 2.62-2.46 (m, 2H), 1.66-1.53 (m, 2H), 1.43 (qd, J=15.0, 7.3 Hz, 2H), 0.96 (t, J=7.3 Hz, 3H); MS (ESI+) m/z 236.0 (M+H)+.
Sources & evidence
- ORD record
- ord-a5bdcbfb0b8446778ab60b08b20309a2
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346795B2
Reaction notes
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