Reaction #531867

Reaction equation

water

1-adamantyl isocyanate

trans-4-aminocyclohexanol hydrochloride

triethylamine

→

trans-1-(4-Hydroxy-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 methanol/water

Procedure

To a solution of 1-adamantyl isocyanate (10 g, 56.4 mmol) and trans-4-aminocyclohexanol hydrochloride (10.3 g, 67.7 mmol) in DMF (300 mL) was added triethylamine (6.9 g, 67.7 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 methanol/water. Yield: 15.5 g (94% of theory). M.P.: 254° C. 1H NMR (300 MHz, DMSO-d6): δ 5.48 (d. J=9 Hz, 1H), 5.38 (s, 1H), 4.48 (d, J=4.7 Hz, 1H), 3.42-3.28 (m, 1H), 3.28-3.13 (m, 1H), 2.02-1.93 (m, 3H), 1.87-1.68 (m, 9H), 1.63-1.54 (m, 7H), 1.24-0.93 (4H).

Source