Réaction #531897

Équation de réaction

trans-4-amino-cyclohexylcarboxylic acid methyl ester hydrochloride

MgSO4

benzaldehyde

NaBH4

→

4-benzylamino-cyclohexanecarboxylic acid methyl ester

Rendement 47.0%

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 (2×500 mL)
3. 3
   Autredried
4. 4
   Concentrationconcentrated
5. 5
   AutreThe resulting solid is purified by flash chromatography (gradient elution: 0-100% EtOAc/Hep) which

Mode opératoire

To a solution of trans-4-amino-cyclohexylcarboxylic acid methyl ester hydrochloride (4.5 g, 23.24 mmol) in MeOH (30 mL) is added TEA (1.3 mL, 9.339 mmol), MgSO4 (4.2 g, 34.88 mmol), and benzaldehyde (2.5 mL, 24.74 mmol). The mixture stirs 1 h. The mixture is then cooled to 0° C. and NaBH4 (5.0 g, 132.2 mmol) is added portionwise over 0.5 h. The mixture stirs 1 h at ambient temperature. Then H2O (200 mL) is added and the mixture is extracted with EtOAc (2×500 mL), dried and concentrated. The resulting solid is purified by flash chromatography (gradient elution: 0-100% EtOAc/Hep) which affords 2.7 g of 4-benzylamino-cyclohexanecarboxylic acid methyl ester. LC/MS: [M+H]+ 248, Rt=0.82 min (method 11).

Source