Synthesis of Dysibetaine

Structure of Dysibetaine

C9H16N2O4

Principal investigatorYoshihisa Kobayashi
Publication year2009
Synthesis typeTotal
Number of steps 11 (linear)
References
Part 1 of 1
intermediate structure
Cl3CCH(OH)2
intermediate structure
SOCl2
Reflux, 60 h
intermediate structure
CH2N2, HCl
Et2O
RT, 60 min, 97% (3 steps)
intermediate structure
NaN3, NaI
MeCN
RT, 90 min, 99%
intermediate structure + intermediate structure
TMS2NH
HFIPA
RT, ON, 85%
See the Ugi Reaction
intermediate structure
Ac2O, Pyr
CH2Cl2
RT, 24 h, 92%
intermediate structure
Camphorsulfonic acid
PhH
60 °C, 90 min, 29%
"Also isolated was the C5-epimer (50 % yield)."
intermediate structure
NaOH
MeOH, H2O
RT, 36 h, 100%
intermediate structure
CH2O, H2, Pd/C, HCl
MeOH, H2O
RT, 18 h, 99%
intermediate structure
MeI
THF
RT, 24 h, 84%
intermediate structure
Dowex 550A
MeOH
100%
intermediate structure