Substitution (Mesylate)

(Cyanide)

Examples:

Example 1

To a solution of the SM (14.0 g, 40.6 mmol) in DMF (150 mL) at 0 C was added 18-Crown-6 (550 mg) and NaCN (5.3 g, 81.0 mmol). The reaction was stirred at RT for 16 h, after which time the mixture was quenched with H2O. The mixture was extracted with EtOAc, dried (Na2SO4), and concentrated in vacuo. The resulting material was purified by silica gel column chromatography (10% EtOAc/hexane) to provide the product as an off-white solid. [3.8 g, 34%]

[Patent Reference: WO2014149164, page 234, (23.7 MB)]