Réaction #531895

Équation de réaction

H2O

4-benzylamino-cyclohexanecarboxylic acid tert-butyl ester

t-butyl bromoacetate

Cs2CO3

→

4-(benzyl-tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl ester

Rendement 34.1%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Extractionis extracted with EtOAc (2×100 mL)
2. 2
   Séchagedried with sodium sulfate
3. 3
   Concentrationconcentrated
4. 4
   AutreThe resulting solid is purified by flash chromatography (gradient elution: 0-20% EtOAc/Hep) which

Mode opératoire

To a solution of 4-benzylamino-cyclohexanecarboxylic acid tert-butyl ester (630 mg, 2.180 mmol) in DMF (20 mL) is added t-butyl bromoacetate (1 mL, 6.856 mmol) and Cs2CO3 (1.0 g, 3.069 mmol). The mixture stirs for 2 h. Then H2O (50 mL) is added the mixture is extracted with EtOAc (2×100 mL), dried with sodium sulfate and concentrated. The resulting solid is purified by flash chromatography (gradient elution: 0-20% EtOAc/Hep) which affords 300 mg of 4-(benzyl-tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl ester. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.24 (m, 5 H), 1.38 (m, 18 H), 1.86 (m, 4 H), 2.09 (m, 1 H), 3.14 (m, 2 H), 3.71 (m, 2 H), 7.29 (m, 5 H).

Source