Reacción #160372

Ecuación de reacción

sodium triacetoxyborohydride

3-[(4-Methyl-cyclohexanecarbonyl)-piperidin-4-yl-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

benzaldehyde

→

3-[(1-Benzyl-piperidin-4-yl)-(4-methyl-cyclohexanecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

Rendimiento 61.5%

Disolventes

dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched with a saturated NaHCO3 solution
2. 2
   Extracciónextracted with Ethyl acetate (3×5 ml)
3. 3
   LavadoThe combined extracts were then washed with brine
4. 4
   Otrodried on Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue was purified by preparative chromatography (50% EtOAc/Hex)

Procedimiento

To 3-[(4-Methyl-cyclohexanecarbonyl)-piperidin-4-yl-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (43 mg, 0.098 mmol) in dichloroethane (1.0 ml) was added benzaldehyde (15 ul, 0.146 mmol), followed by sodium triacetoxyborohydride (41 mg, 0.195 mmol). The reaction mixture was stirred at room temperature for 4 h, quenched with a saturated NaHCO3 solution, and then extracted with Ethyl acetate (3×5 ml). The combined extracts were then washed with brine and dried on Na2SO4, filtered and concentrated. The residue was purified by preparative chromatography (50% EtOAc/Hex) to give 32 mg (61%) of 3-[(1-Benzyl-piperidin-4-yl)-(4-methyl-cyclohexanecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester.

Fuente