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
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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%
