Reaktion #531897

Reaktionsgleichung

trans-4-amino-cyclohexylcarboxylic acid methyl ester hydrochloride

MgSO4

benzaldehyde

NaBH4

→

4-benzylamino-cyclohexanecarboxylic acid methyl ester

Ausbeute 47.0%

Lösungsmittel

H2O

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITThe mixture stirs 1 h at ambient temperature
2. 2
   Extraktionthe mixture is extracted with EtOAc (2×500 mL)
3. 3
   Sonstigedried
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe resulting solid is purified by flash chromatography (gradient elution: 0-100% EtOAc/Hep) which

Vorschrift

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).

Quelle