4292
X. E. Hu et al. / Tetrahedron Letters 43 (2002) 4289–4293
Figure 2.
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15. A typical procedure for the addition reaction: To a
suspension of CuI (4.4 mg, 0.0231 mmol) in anhydrous
THF (2.5 mL) was slowly added 1.0 M EtMgBr in THF
(0.93 mL, 0.924 mmol) at −30°C. After stirring at that
temperature for 15 min, a solution of the aziridine (7) (85
mg, 0.231 mmol) in THF (2.5 mL) was added at the same
temperature and then the mixture was slowly warmed to
0°C in 2 h, at which time no starting aziridine was
detected by TLC, HPLC and MS analyses. Water (2 mL)
was added to quench the reaction and the mixture was
extracted with ethyl acetate (2×10 mL), dried over anhy-
drous MgSO4 and evaporated. The crude product was
purified by flash chromatography using ethyl ace-
tate:hexanes (1:1 and then 1:0) (Rf=0.10) to afford 75 mg
(82%) of 4-ethyl-piperidine product (9b) as a colorless oil.
9. Hu, X. E.; Kim, N. K.; Ledoussal, B. Regio- and Stereo-
controlled Synthesis of trans-3-Amino-4-Substituted Pip-
eridines from A Piperidinyl Aziridine; 2nd Singapore
International Chemical Conference (SICC), Dec. 2001.