Dichloromethane → HCID 71187339, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(((tert-butyldiphenylsilyl)oxy)methyl)-3-tosyl-3-azabicyclo[4.1.0]heptane (D12) (3.12 g, 6 mmol) in MeOH (430 ml), under a nitrogen atmosphere, magnesium turnings (previously flame dried) (8.46 g, 348 mmol) and NH4Cl (8.9 g, 168 mmol) were added sequentially and the mixture was stirred at 23° C. Two further additions of magnesium (4.3 g), each one after 2 hrs stirring, were done. DCM (210 ml) and NH4Cl sat. sol. (285 ml) were added to the reaction mixture. The formed emulsion was filtered through a celite pad. The organic layer was separated and washed with brine (2×55 ml). The combined organic layers were evaporated and the resulting residue was purified by SPE-SCX (20 g) cartridge. Collected ammonia fractions after solvent evaporation afforded the title compound (D13) (1.65 g).

Provenance & Evidence