Reaktion #531894

Reaktionsgleichung

4-amino-cyclohexanecarboxylic acid tert-butyl ester

MgSO4

benzaldehyde

NaBH4

→

4-benzylamino-cyclohexanecarboxylic acid tert-butyl ester

Ausbeute 100.9%

Lösungsmittel

H2O

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITThe mixture stirs 1 h at ambient temperature
2. 2
   Extraktionthe mixture is extracted with EtOAc (2×50 mL)
3. 3
   Sonstigedried
4. 4
   Einengenconcentrated

Vorschrift

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).

Quelle