Mannich Reaction

Mechanism of the Mannich Reaction

Sample reactions

AcOH, CH2O, Me2NH
Dioxane , H2O
RT, 2 h, 92%


(CF3CO)2O
CF3CO2H
Reflux, 14 h, 67% (2 steps)


2,6-Di-tert-butyl-4-methylpyridine, BCl3
CH2Cl2
RT, 15 h, 85%



TMS2NLi
Et2O
-78 °C, 3 h, 78%
"Also isolated was the C5-epimer (8 % yield)."


TsOH
PhH
RT, 40 h, 58% (3 steps)
"Also isolated was the C2-epimer (18% yield)."


(CH2O)n
3-Methyl-1-butanol
Reflux, 20 h


Dess-Martin Periodinane, Et3N, NaHCO3, H2CN+Me2 I-
CH2Cl2
RT, ON, 97%



DMF
100 °C


BF3.OEt2, HgO
MeOH



i-PrN(Cy)Li, H2CN+Me2 I-
THF
-78 to 0 °C, 8 h, 15%




CF3CO2H
CH2Cl2
-78 °C to RT, 5.5 h, 78%



Et3N, ZnCl2, t-BuOCl
THF
-78 °C to RT, ON



THF
-78 °C to RT, 13 h, 83% (2 steps)




THF
-78 °C to RT, 2 h, 79%


TMS2NLi
THF
-15 °C to RT, 3.5 h, 26%


TMS2NK, 2-Butanone
Et2O
-78 °C, 90 min, 84%


TsOH
PhH
60 °C, 4 h, 74%


H2CN+Me2 I-
CH2Cl2
35 °C, 48 h


CH2O, Me2NH
AcOH
RT, 2 h
