Réaction #2254209

Équation de réaction

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

Solvants

CH2Cl2

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source