Synthesis of Suaveoline

Structure of Suaveoline

C20H21N3

Principal investigatorJames M. Cook
Publication year1989
Synthesis typeTotal
Number of steps 20 (linear)
References
Part 1 of 1
intermediate structure
MeI, Na
NH3
intermediate structure
HCl
MeOH
Reflux
intermediate structure
NaBH4, PhCHO
MeOH
73% (3 steps)
intermediate structure + intermediate structure
Dioxane , PhH
Reflux
intermediate structure
HCl
MeOH
Reflux, , 88% (2 steps)
intermediate structure
NaH
MeOH, PhMe
Reflux
intermediate structure
HCl
AcOH
Reflux, , 83% (2 steps)
intermediate structure
i-Pr2NLi, PhSOCH2Cl
THF
-78 °C
intermediate structure
KOH
H2O, THF
RT, 24 h, 95% (2 steps)
intermediate structure
LiClO4, n-Bu3PO
PhMe
Reflux, 60 min, 80%
intermediate structure
LiAlH4
Et2O
-20 °C, , 91%
intermediate structure + intermediate structure
2,4,6-Trimethylbenzoic acid
125 °C, 3 h, 79%
intermediate structure
LiAlH4
Et2O
-20 °C
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C
See the Swern Oxidation
intermediate structure
(CH2OH)2, TsOH
PhH
Reflux, , 60% (3 steps)
intermediate structure
  1. H2O
  2. H2O2
  3. NaOH
  4. 9-BBN
THF
35 °C, 60 min, 91%
intermediate structure
(PhSeO)2O
PhCl
120 °C, 15 min, 58%
intermediate structure
HCl
H2O, THF
RT, 24 h
intermediate structure
NH2OH.HCl
EtOH
Reflux, , 40% (2 steps)
intermediate structure
H2, Pd/C
MeOH
69%
intermediate structure