Synthesis
General procedure for the synthesis of trans-2-benzylaminocyclohexanol from cyclohexene oxide and benzylamine: cyclohexene oxide (20 g, 204 mmol) was mixed with benzylamine (44 g, 411 mmol), and the reaction was carried out for 6 hours at 80 °C. After completion of the reaction, the excess benzylamine was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent being a chloroform solution of 5-10% methanol to give (1RS,2RS)-trans-2-benzylaminocyclohexanol (26 g, 127 mmol, 62% yield) as white crystals.
References
[1] Tetrahedron Letters, 2008, vol. 49, # 9, p. 1546 - 1550
[2] Tetrahedron, 2011, vol. 67, # 47, p. 9214 - 9218
[3] Journal of Organic Chemistry, 2007, vol. 72, # 10, p. 3713 - 3722
[4] Tetrahedron Letters, 1990, vol. 31, # 32, p. 4661 - 4664
[5] Synthetic Communications, 2001, vol. 31, # 21, p. 3295 - 3302
