Benzaldehyde → 4-Benzylamino-cyclohexanecarboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Benzaldehyde	HCID 240	—
Reactant	Sulfuric acid magnesium salt (1:1)	HCID 24083	—
Reactant	Sodium borohydride	HCID 4311764	—
Reactant	tert-Butyl 4-aminocyclohexane-1-carboxylate	HCID 18698345	—
Solvent	Methanol	HCID 887	—
Solvent	Water	HCID 962	—
Product	4-Benzylamino-cyclohexanecarboxylic acid tert-butyl ester	HCID 68724841	100.9%

Reaction Conditions

Temperature	0 °C

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08691756B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-a2d11f56ae6242f9897c3dc217544cbd
Source note	uspto-grants-2014_04