Methyl-2-(tert-butoxycarbonyl)-3-(7-methyl-2-[{2-[trimethylsilyl]ethoxy}methyl]-2H-indazol-5-yl)acrylate → (+/-)-Methyl-2-(tert-butoxycarbonyl)-3-(7-methyl-2-[{2-[trimethylsilyl]ethoxy}methyl]-2H-indazol-5-yl)propanoate
Reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:5][C:6]1[CH:14]=[C:13]([CH3:15])[C:12]2[C:8](=[CH:9][N:10]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:11]=2)[CH:7]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:31])[CH:4]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:5][C:6]1[CH:14]=[C:13]([CH3:15])[C:12]2[C:8](=[CH:9][N:10]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:22])([CH3:21])[CH3:23])[N:11]=2)[CH:7]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of methyl-2-(tert-butoxycarbonyl)-3-(7-methyl-2-[{2-[trimethylsilyl]ethoxy}methyl]-2H-indazol-5-yl)acrylate (3.7 g, 8.0 mmol) in methanol (20 mL) was flushed with nitrogen (2×), and treated with palladium (10% on charcoal, 0.37 g). The flask was flushed with hydrogen and was shaken in a parr apparatus overnight at 60 psi. The reaction was flushed with nitrogen, filtered through celite, and concentrated. Column chromatography gave 2.3 g (63%). 1H-NMR (CDCl3, 500 MHz) δ −0.03 (s, 9H), 0.92-0.97 (m, 2H), 1.41 (s, 9H), 2.59 (s, 3H), 3.00-3.17 (m, 2H), 3.59-3.67 (m, 2H), 3.71 (s, 1H), 4.54-4.64 (m, 1H), 4.92-5.01 (m, 1H), 5.71 (s, 2H), 6.82 (s, 1H), 7.12-7.19 (m, 2H), 8.01 (s, 1H). Mass spec.: 464.29 (MH)+.
Workup
- customThe flask was flushed with hydrogen
- customThe reaction was flushed with nitrogen
- filtrationfiltered through celite
- concentrationconcentrated
- customColumn chromatography gave 2.3 g (63%)
Sources & evidence
- ORD record
- ord-66c9afb4a0df48a58934b4f60dd89d3f
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07569578B2
Reaction notes
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