Réaction #531857

Équation de réaction

4-(3-adamantan-1-yl-ureido)butyric acid

K2CO3

iodomethane

→

883

Rendement 95.0%

4-(3-Adamantan-1-yl-ureido) butyric Acid Methyl Ester

Rendement 95.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   ExtractionThen the product was extracted with ether (20 mL)
2. 2
   Lavagethe ether was washed with 1 N NaOH aqueous solution (20 mL) and brine (20 mL)
3. 3
   Séchagedried over Na2SO4
4. 4
   Autreevaporated

Mode opératoire

A mixture of 4-(3-adamantan-1-yl-ureido)butyric acid 822 (0.15 g, 0.54 mmol), K2CO3 (0.09 g, 0.64 mmol), and iodomethane (0.04 mL, 0.59 mmol) in DMF (20 mL) was stirred at room temperature for 20 h. Then the product was extracted with ether (20 mL), and the ether was washed with 1 N NaOH aqueous solution (20 mL) and brine (20 mL), dried over Na2SO4, and evaporated to afford 0.15 g (95%) of 883: 1H NMR (CDCl3) 1.66-1.68 (6H, m), 1.81 (2H, quint, J=6.9 Hz), 1.94-1.97 (6H, m), 2.05-2.07 (3H, m), 2.37 (2H, t, J=6.9 Hz), 3.16 (2H, q, J=6.9 Hz), 3.68 (3H, s), 4.09 (1H, s), 4.25 (1H, s); LC-MS (ESI) m/z calcd for C16H26N2O3 [M+H]+ 295.19. found [M+H]+ 295.24; mp 114 C. Anal. (C16H26N2O3) C, H, N.

Source