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温度

0 °C

(+,−) Cis-2-Phenyl-cyclopentylamine (0.43 g, 2.7 mmol, from preparations 5 or 7) was dissolved in 15 mL of methylene chloride and cooled to 0° C. under nitrogen. 0.52 mL (3.5 mmol) of DBU was added followed by 0.39 mL (3.5 mmol) of isopropylsulfonyl chloride. Stirring was allowed to continue for 3 days while warming to room temperature. The reaction was washed with 1N HCl and the organic phase dried over sodium sulfate. Filtered, and concentrated in vacuo to a crude brown solid which was a 4:1 mixture of cis:trans by NMR. The isomers were purified by radial chromatography eluting with methylene chloride. 195 mg (27%) of the title compound (cis isomer) was isolated as a white solid as well as 15 mg of the more polar trans isomer. The NMR was consistent with the assigned structure.

1. temperaturewhile warming to room temperature
2. washThe reaction was washed with 1N HCl
3. dry with materialthe organic phase dried over sodium sulfate
4. filtrationFiltered
5. concentrationconcentrated in vacuo to a crude brown solid which
6. additiona 4:1 mixture of cis
7. customThe isomers were purified by radial chromatography
8. washeluting with methylene chloride