Reaction #531869

Reaction equation

ester

trans-4-Nitro-benzoic acid 4-(3-tricyclo[3.3.1.13,7]decan-1-yl-ureido)-cyclohexyl ester

NaOH

→

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

Solvents

THF

Conditions

Workup

1. 1
   Otherwas quenched by addition of 1N HCl solution (5.5 mL)
2. 2
   FiltrationThe resulting white precipitate was collected by filtration
3. 3
   Otherrecrystallized from methanol/water

Procedure

To a solution of ester 1076 (1 g, 2.3 mmol) in THF (100 mL) was added 1N NaOH solution (4.6 mL, 4.6 mmol) at room temperature. The reaction mixture was stirred overnight, at which time the reaction was quenched by addition of 1N HCl solution (5.5 mL). The resulting white precipitate was collected by filtration and recrystallized from methanol/water. Yield: 0.63 g (95% of theory). M.P.: 205° C. 1H NMR (300 MHz, DMSO-d6): δ 5.67 (d, J=8.2 Hz, 1H), 5.45 (s, 1H), 4.41 (s, 1H), 3.63-3.51 (m, 1H), 3.46-3.36 (m, 1H), 2.00-1.92 (m, 3H), 1.87-1.72 (m, 6H), 1.66-1.28 (m, 14H).

Source