Reaction #531857

Reaction equation

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

K2CO3

iodomethane

→

883

Yield 95.0%

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

Yield 95.0%

Solvents

DMF

Conditions

Workup

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

Procedure

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