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Wynberg, H.5
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12
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85033758283
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note
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The enantiomeric excess of both starting carbamates were evaluated by chiral HPLC and were found to be 99.6% ee for the (L) isomer and 99% ee for the (D) isomer. Experiments were performed at ambient temperature and with UV detection at 220 nm. A chiralcel OD column (250 x 4.6 mm I.D., Interchim, Montluçon, France) was used with the following mobile phase: n-hexane - 2-propanol 90 - 10; flow rate, 0.5 ml/min.
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13
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85033755870
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note
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HPLC conditions for the ureas: Chiralcel OD (250 x 4.6 mm I.D.), n-hexane - ethanol 70 - 30 modified with 0.1% diethylamine, 220 nm, 0.5 ml/min.
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17
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85033750482
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note
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Method A: A THF solution of the amine anion prepared from amine 2 and n-BuLi is added dropwise at room temperature to a solution of carbamate 1 in THF. The reaction is then heated at reflux for the given time. Method B: The carbamate 1 and the amine 2 are dissolved in the solvent at room temperature prior to the addition of the base. The reaction is then heated at reflux for the given time. Method C: A THF solution of the amine anion prepared from amine 2 and n-BuLi is added dropwise at -78°C to a solution of carbamate 1 in THF. The reaction is then heated at reflux for the given time.
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