Reacción #2254205

Ecuación de reacción

2-[4-(4-fluorophenyl)oxan-4-yl]ethan-1-amine

benzaldehyde

→

benzyl({2-[4-(4-fluorophenyl)oxan-4-yl]ethyl})amine

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe reaction mixture was filtered
2. 2
   Concentraciónconcentrated
3. 3
   workup.DISSOLUTIONThe residue was dissolved in 5 ml MeOH at 0° C.
4. 4
   workup.ADDITIONNaBH4 added in one portion (51 mg, 1.34 mmol)
5. 5
   workup.STIRRINGThe reaction was stirred at 0° C. for 1 h
6. 6
   OtroThe solution was then quenched with H2O (10 ml)
7. 7
   Extracciónextracted with CH2Cl2 (3×20 ml)
8. 8
   Lavadowashed with brine (10 ml)
9. 9
   Otrodried over NA2SO4
10. 10
    OtroPurified by normal phase SiO2 chromatography (0 to 10% MeOH/CH2Cl2)

Procedimiento

To a solution of 2-[4-(4-fluorophenyl)oxan-4-yl]ethan-1-amine (250 mg, 1.12 mmol) in anhydrous CH2Cl2 (5 ml) and NA2SO4 (159 mg, 1.12 mmol) at rt was added benzaldehyde (0.17 ml, 1.68 mmol). The reaction was stirred overnight. The reaction mixture was filtered and concentrated. The residue was dissolved in 5 ml MeOH at 0° C. and NaBH4 added in one portion (51 mg, 1.34 mmol). The reaction was stirred at 0° C. for 1 h. The solution was then quenched with H2O (10 ml), extracted with CH2Cl2 (3×20 ml), washed with brine (10 ml) and dried over NA2SO4. Purified by normal phase SiO2 chromatography (0 to 10% MeOH/CH2Cl2) to give benzyl({2-[4-(4-fluorophenyl)oxan-4-yl]ethyl})amine as a colorless oil (200 mg, 60%, m/z: 314.2 [M+H]+ observed).

Fuente