(2S)-2-(1-methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]-1-[2-(methylsulfonyl)-ethyl]piperazine → 4-{(3S)-3-(1-methylethyl)-4-[2-(methylsulfonyl)ethyl)-1-piperazinyl]-2-(methyloxy)aniline
Reaction equation
[CH3:1][CH:2]([C@H:4]1[CH2:9][N:8]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([O:19][CH3:20])[CH:11]=2)[CH2:7][CH2:6][N:5]1[CH2:21][CH2:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH3:3]>CCO.[Pd]>[CH3:3][CH:2]([C@@H:4]1[N:5]([CH2:21][CH2:22][S:23]([CH3:26])(=[O:24])=[O:25])[CH2:6][CH2:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([O:19][CH3:20])[CH:11]=2)[CH2:9]1)[CH3:1]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
(2S)-2-(1-Methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]-1-[2-(methylsulfonyl)-ethyl]piperazine (0.382 g, 0.991 mmol) was dissolved in 15 mL of EtOH with stirring. 10% Palladium on carbon (0.105 g, 0.0987 mmol) was added, and the reaction was placed under 1 atm of H2 using a balloon. The reaction was stirred for 8 h and filtered through celite washing with EtOAc. The filtrate was concentrated in vacuo to provide the title compound of step G (0.349 g, 0.982 mmol, 99%). 1H NMR (400 MHz, DMSO-d6) δ 6.47 (d, J=8.4 Hz, 1H), 6.41 (d, J=2.4 Hz, 1H), 6.25 (dd, J=8.4, 2.4 Hz, 1H), 4.17 (br. s., 2H), 3.69 (s, 3H), 3.28-3.39 (m, 1H), 3.04-3.23 (m, 4H), 2.98 (s, 3H), 2.90 (d, J=11.0 Hz, 1H), 2.70-2.81 (m, 1H), 2.48-2.58 (m, 1H), 2.30-2.44 (m, 2H), 2.16-2.25 (m, 1H), 2.02-2.15 (m, 1H), 0.91 (d, J=7.0 Hz, 3H), 0.83 (d, J=6.8 Hz, 3H).
Workup
- stirringThe reaction was stirred for 8 h
- filtrationfiltered
- washthrough celite washing with EtOAc
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-c68466a72b714a76882905d8ef388aad
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093239B2
Reaction notes
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