Water → N-Benzyl-N-{(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-[(triethylsilyl)oxy]ethyl}amine
Reaction equation
Br[CH2:2][C@H:3]([O:16][Si:17]([CH2:22][CH3:23])([CH2:20][CH3:21])[CH2:18][CH3:19])[C:4]1[CH:15]=[CH:14][C:7]2[O:8][C:9]([CH3:13])([CH3:12])[O:10][CH2:11][C:6]=2[CH:5]=1.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O.C(OCC)C>O1CCOCC1>[CH2:24]([NH:31][CH2:2][C@@H:3]([C:4]1[CH:15]=[CH:14][C:7]2[O:8][C:9]([CH3:13])([CH3:12])[O:10][CH2:11][C:6]=2[CH:5]=1)[O:16][Si:17]([CH2:22][CH3:23])([CH2:20][CH3:21])[CH2:18][CH3:19])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1Participants
Conditions
- Temperature
- 105 °C
Procedure
A mixture of {[(1R)-2-bromo-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethyl]oxy}(triethyl)silane (130 g) and benzylamine (177 ml) in 1,4-dioxane (650 ml) was heated at 105° C. with stirring overnight. The mixture was then cooled to room temperature and water (150 ml) and diethyl ether (1200 ml) added. The layers were separated and the ethereal layer was washed with saturated ammonium chloride solution (3×600 ml), saturated sodium bicarbonate solution (200 ml) and then brine (200 ml). The solution was dried over anhydrous Na2SO4 before being filtered and concentrated under reduced pressure to give the title compound (129.9 g) as an oil, δ (CDCl3) 7.22 (5H, m), 7.02 (1H, d, J 8.7 Hz), 6.86 (1H, s), 6.68 (1H, d, J 8.3 Hz), 4.75 (2H, s), 4.69 (1H, m), 3.73 (2H, s), 2.70 (2H, m), 1.46 (6H, s), 0.79 (9H, m), 0.44 (6H, m).
Workup
- temperatureThe mixture was then cooled to room temperature
- customThe layers were separated
- washthe ethereal layer was washed with saturated ammonium chloride solution (3×600 ml), saturated sodium bicarbonate solution (200 ml)
- dry with materialThe solution was dried over anhydrous Na2SO4
- filtrationbefore being filtered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-06146bf501ea45bfbcbf2fc1939a6f43
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07144908B2
Reaction notes
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