Reacción #2254209

Ecuación de reacción

sodium triacetoxyborohydride

2-[2,2-dimethyl-4-(4-methylphenyl)oxan-4-yl]acetaldehyde

3-methylbenzylamine

acetic acid

→

{2-[2,2-dimethyl-4-(4-methylphenyl)oxan-4-yl]ethyl}[(3-methylphenyl)methyl]amine

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe resulting mixture was stirred at rt for 18 h
2. 2
   ConcentraciónThe mix was concentrated
3. 3
   workup.DISSOLUTIONdissolved in MeOH
4. 4
   Otropurified by HPLC

Procedimiento

A mixture of 2-[2,2-dimethyl-4-(4-methylphenyl)oxan-4-yl]acetaldehyde (61.6 mg, 0.25 mmol), 3-methylbenzylamine (63 μl, 0.5 mmol) and acetic acid (50 μl, 8.6 mmol) in CH2Cl2 (3 ml) was stirred at rt for 1 h before it adding sodium triacetoxyborohydride (106 mg, 0.50 mmol). The resulting mixture was stirred at rt for 18 h. The mix was concentrated and dissolved in MeOH and purified by HPLC to give {2-[2,2-dimethyl-4-(4-methylphenyl)oxan-4-yl]ethyl}[(3-methylphenyl)methyl]amine as a white solid (35 mg, 40%, m/z: 352.3 [M+H]+ observed).

Fuente