Réaction #531894

Équation de réaction

4-amino-cyclohexanecarboxylic acid tert-butyl ester

MgSO4

benzaldehyde

NaBH4

→

4-benzylamino-cyclohexanecarboxylic acid tert-butyl ester

Rendement 100.9%

Solvants

H2O

MeOH

Conditions de réaction

Traitement

1. 1
   workup.WAITThe mixture stirs 1 h at ambient temperature
2. 2
   Extractionthe mixture is extracted with EtOAc (2×50 mL)
3. 3
   Autredried
4. 4
   Concentrationconcentrated

Mode opératoire

To a solution of 4-amino-cyclohexanecarboxylic acid tert-butyl ester (500 mg, 2.500 mmol) in MeOH (3 mL) is added TEA (140 uL, 1.000 mmol), MgSO4 (452 mg, 3.750 mmol), and benzaldehyde (278 uL, 2.750 mmol). The mixture stirs 1 h. The mixture is then cooled to 0° C. and NaBH4 (568 mg, 15.00 mmol) is added portionwise over 10 min. The mixture stirs 1 h at ambient temperature. Then H2O (20 mL) is added and the mixture is extracted with EtOAc (2×50 mL), dried and concentrated to affords 730 mg of 4-benzylamino-cyclohexanecarboxylic acid tert-butyl ester. LC/MS: [M+H]+ 290, Rt=0.80 min (method 6).

Source