Iodine → HCID 131729008, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 975 mg of magnesium, 100 μL of bromoethane, and 20 μL of tetrahydrofuran, a catalyst amount of iodine was added, and the mixture was stirred for about 10 minutes until the brown color from iodine disappears. Thereto, 20 mL of a tetrahydrofuran solution containing 5.9 g of 4-chloro-1-methylpiperidine was added, and heated for 2.5 hours under reflux. Thus produced white suspension was cooled to 0° C., and 10 mL of a tetrahydrofuran solution containing 2 g of the compound [15-1] was added thereto. After the overnight stirring under gradually heating back to room temperature, a saturated aqueous solution of ammonium chloride was added thereto, and extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine in that order, and dried over anhydrous magnesium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=100/0-90/10), to obtain 2.27 g of tert-butyl((1S)-1-{4-[hydroxy(1-methylpiperidin-4-yl)methyl]phenyl}ethyl)carbamate [23-1] (hereinafter, referred to as the compound [23-1]).

Provenance & Evidence