Hydrochloric Acid → HCID 54117741, compound

Participants

Reaction Conditions

Reaction Steps

2.8 mmol of a 1.4M sec-butyllithium solution in cyclohexane/isopentane were added to a solution, cooled to -78° C., of 680 mg (2.8 mmol) of (-)-sparteine in 8 ml of anhydrous ether. After stirring at -78° C. for 10 min, a solution of 543 mg (2.0 mmol) of the carbamate from Example 1 of the formula II in 2 ml of ether was added dropwise and the reaction mixture was stirred at -78° C. for 4 hours. After addition of 426 mg (3.0 mmol) of methyl iodide in 2 ml of ether, the reaction was subsequently stirred for 16 hours to complete the reaction, the mixture slowly warming to room temperature. To work up the reaction mixture, it was warmed to room temperature and poured into 10 ml of ether and 10 ml of 2N HCl. The organic phase was separated off, the aqueous phase was extracted three times with 20 ml of ether each time and the combined organic phases were deacidified and dried over solid sodium hydrogen sulphate and sodium sulphate in the amount ratio 1:2. After filtration and removal of the solvent in vacuo, the crude product was purified by chromatography on silica gel (ether/n-pentane 1:10). 491 mg (87%) of the title compound were obtained as a colorless oil of 95% ee. RF =0.74 (silica gel, ether/pentane 1:1), [α]D19 =+15.40 (c=1.20, acetone).

Provenance & Evidence