Bromoacetic Acid → 2-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

Temperature

-15 °C

Bromoacetic acid (0.50 g, 3.6 mmol) was dissolved in anhydrous tetrahydrofuran (20 ml), and the solution was stirred at −15° C. under a nitrogen atmosphere. N-Methylmorpholine (0.40 ml, 3.6 mmol) and isobutyl chlorocarbonate (0.45 ml, 3.5 mmol) were added to the solution. Then a solution of a free base of 2-(1-adamantyl)-N-pentylethylamine hydrochloride (Intermediate No. 1-1, 1.0 g, 3.5 mmol) in anhydrous tetrahydrofuran (20 ml) was added dropwise to the mixture. The whole was stirred at 0° C. for 1.5 hours, then a saturated aqueous sodium hydrogencarbonate solution (70 ml) and ethyl acetate (70 ml) were added to the reaction mixture to distribute it. The ethyl acetate layer was washed with water (70 ml) and a saturated aqueous sodium chloride solution (70 ml) successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 2-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide (1.3 g, quantitatively) as an oily matter.

1. stirringThe whole was stirred at 0° C. for 1.5 hours
2. washThe ethyl acetate layer was washed with water (70 ml)
3. dry with materiala saturated aqueous sodium chloride solution (70 ml) successively, dried over anhydrous magnesium sulfate
4. concentrationconcentrated under reduced pressure

ORD record

ord-e19bd88eb6a84b79b364774825249667

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07741346B2