Synthesis of Echitamidine

Structure of Echitamidine

C20H24N2O3

Principal investigatorJoan Bosch
Publication year1997
Synthesis typeTotal
Number of steps 17 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
K2CO3
DMSO
85-90 °C, 4 h, 72%
intermediate structure
K2CO3, AllylBr
Acetone
Reflux, 3 h, 85%
intermediate structure
PhMe
180-190 °C, 12 h, 80%
intermediate structure
O3
CH2Cl2
-78 °C, 5 h
intermediate structure
NaBH3CN, MeNH2.HCl
MeOH
RT, 4 h, 36%
"Also isolated was the C7a-epimer (26 % yield)."
intermediate structure
ClCO2CH(Cl)CH3, Proton Sponge
DCE
0 °C to Reflux, 3.5 h, 100%
intermediate structure
TMS2NH, TMSI
CH2Cl2, Pentane
-20 °C, 6 h, 100%
intermediate structure
(PhSe)2, PhSeCl
THF
-35 °C to RT, 4.5 h, 70%
intermediate structure
  1. O3
  2. i-Pr2NH
CH2Cl2
-78 °C to RT, , 72%
intermediate structure
MeOH
Reflux, 3 h, 100%
intermediate structure
Et3N, Methyl vinyl ketone
MeOH
RT, 105 min, 74%
intermediate structure
Me3N+Bn HO-
DME
-20 °C, 2.5 h, 44%
"Also isolated was the C2-epimer (14 % yield)."
intermediate structure
BF3.OEt2, (CH2SH)2
AcOH
RT, 24 h, 80%
intermediate structure
  1. i-Pr2NLi
  2. MeO2CCN
HMPA, THF
-78 °C to RT, 3.5 h, 50%
intermediate structure
BF3.OEt2, HgO
H2O, THF
RT, 35 min, 86%
intermediate structure
H2, HCl, Pd/C
MeOH
RT, 2 h, 80%
intermediate structure
NaBH4
MeOH
0 °C to RT, 3 h, 75%
intermediate structure