2-(3-{2-[2-(2-{2-Azidoethoxy}ethoxy)ethoxy]ethoxy}-4,5-dimethoxyphenyl)-1,3-dioxolane → 2-(3-{2-[2-(2-{2-Aminoethoxy}ethoxy)ethoxy]ethoxy}-4,5-dimethoxyphenyl)-1,3-dioxolane
Reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH:26]2[O:30][CH2:29][CH2:28][O:27]2)[CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23])=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH:26]2[O:27][CH2:28][CH2:29][O:30]2)[CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Fifty mg of Pd/C was added to a solution of 7.18 g (16.8 mmol) 2-(3-{2-[2-(2-{2-azidoethoxy}ethoxy)ethoxy]ethoxy}-4,5-dimethoxyphenyl)-1,3-dioxolane 11 in 100 ml ethanol. The mixture was stirred at ambient temperature under a hydrogen atmosphere overnight, filtered and purified by silica gel column chromatography to give 5.69 g (14.2 mmol, 84%) of the product as a clear oil. 1H-NMR (CDCl3) δ=6.73 (dd, 2H, J=5.2 Hz, J=1.7 Hz), 5.72 (s, 1H), 4.19 (m, 2H), 4.11 (m, 2H), 4.02 (m, 2H), 3.86 (s, 3H), 3.84 (s, 3H), 3.87-3.85 (m, 2H), 3.75-3.69 (m, 2H), 3.69-3.59 (m, 6H), 3.57 (t, 1H, J=5.4 Hz), 3.49 (t, 1H, J=5.4 Hz), 2.84 (t, 1H, J=5.2 Hz), 2.79 (t, 1H, J=5.2 Hz), 1.74 (br, 2H) ppm. 13C-NMR δ=153.2, 152.3, 139.1, 133.0, 105.3, 103.5, 103.3, 73.2, 70.6, 70.5, 70.4, 70.1, 69.5, 68.6, 65.0, 60.5, 55.9, 41.6 ppm. MS: m/z=424 [M+Na]+, 402 [M+H]+. HRMS: Calcd. for C19H32NO8+ 402.2122, found 402.2122.
Workup
- filtrationfiltered
- custompurified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-7bfb213d284f42878e0f1aa8b74d11d2
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08212058B2
Reaction notes
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