Reaction #531872

Reaction equation

water

triethylamine

compound 10

cis-4-(4-Fluoro-phenoxy)-cyclohexylamine

1-adamantyl isocyanate

→

cis-1-[4-(4-Fluoro-phenoxy)-cyclohexyl]-3-tricyclo[3.3.1.13,7]decan-1-yl-urea

Solvents

DMF

Conditions

Workup

1. 1
   Otherthe resulting precipitates
2. 2
   Otherwere collected
3. 3
   Washwashed with water
4. 4
   OtherThe crude product was recrystallized from DCM/hexanes

Procedure

To a solution compound 10 in DMF was added 1-adamantyl isocyanate (0.16 g, 0.91 mmol) followed by triethylamine (0.10 g, 1.0 mmol) at 0° C. The reaction mixture was stirred overnight. The reaction mixture was poured into water, and the resulting precipitates were collected and washed with water. The crude product was recrystallized from DCM/hexanes. Yield: 0.31 g (88% of theory). M.P.: 207° C. 1H NMR (300 MHz, CDCl3): δ 6.98-6.91 (m, 2H), 6.84-6.78 (m, 2H), 4.34 (s, 1H), 4.30 (d, J=9.8 Hz, 1H), 4.20 (s, 1H), 3.71-3.56 (m, 1H), 2.13-1.44 (m, 23H).

Source