Synthesis of Suaveoline
C20H21N3
Principal investigator | James M. Cook |
---|---|
Publication year | 1989 |
Synthesis type | Total |
Number of steps | 20 (linear) |
References |
Part 1 of 1
+
+
MeI,
Na
NH3
NaBH4,
PhCHO
MeOH
73% (3 steps)
HCl
AcOH
Reflux, 83% (2 steps)
PhSOCH2Cl,
i-Pr2NLi
THF
-78 °C
KOH
H2O, THF
RT, 24 h, 95% (2 steps)
n-Bu3PO,
LiClO4
PhMe
Reflux, 60 min, 80%
LiAlH4
Et2O
-20 °C, 91%
LiAlH4
Et2O
-20 °C
(CH2OH)2,
TsOH
PhH
Reflux, 60% (3 steps)
- 9-BBN
- NaOH , H2O2 , H2O
THF
35 °C, 60 min, 91%
(PhSeO)2O
PhCl
120 °C, 15 min, 58%
HCl
H2O, THF
RT, 24 h
NH2OH.HCl
EtOH
Reflux, 40% (2 steps)
H2,
Pd/C
MeOH
69%