Dimethyl Sulfate → HCID 18457671, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1′-tert-Butoxycarbonyl-[1,4′]-Bipiperidine 1 (5.1 g, 19.0 mmol), TMEDA (19 mL) in dry Et2O (40 ml) at −78° C. is slowly added a solution of sec-butyllithium (19.0 mL, 24.7 mmol, 1.3 M in cyclohexanes) over a period of 30 min. The mixture is stirred at −78° C. for 3 hr, and then is treated with a solution of dimethylsulfate (3.6 g, 28.5 mmol) in Et2O (5 mL). The cooling bath is removed and the reaction mixture is stirred at ambient temperature for 16 hr. After cooling to 0° C., the reaction mixture is quenched with water, extracted with Et2O (5×100 mL), and the combined ether layers is dried over K2CO3. The solvent is removed under vacuum and the residue is purified by silica gel chromatography (eluting with 40% ethyl acetate in hexane) to give 2.51 g of 1′-tert-butoxycarbonyl-2′-methyl-[1,4′]-bipiperidine, 2.

Provenance & Evidence