Synthesis of Muscopyridine

Structure of Muscopyridine

C16H25N

Principal investigatorGeorge Büchi
Publication year1957
Synthesis typeTotal
Number of steps 12 (linear)
References
J. Am. Chem. Soc. 1957, 79, 5558.
Part 1 of 1
intermediate structure + intermediate structure
KOt-Bu
t-BuOH
Reflux, 22 h, 85%
See the Stobbe Condensation
intermediate structure
PPA
95-98 °C, 3 h
intermediate structure
HCl
AcOH, H2O
Reflux, 19 h, 47% (2 steps)
intermediate structure
Na, NH2NH2
Diethylene glycol
RT to 227 °C, 6 h, 55%
See the Wolff-Kishner Reduction
intermediate structure
HN3, H2SO4
CHCl3, EtOH
50 °C, 3 h
intermediate structure
Pd/C
1-Methylnaphthalene
Reflux, 3.5 h, 18% (2 steps)
intermediate structure
H2O2, H2O
AcOH
80 °C, 45 h, 61% (85% BRSM)
intermediate structure
Ac2O
100 °C, 12 h
intermediate structure
KOH
H2O, MeOH
Reflux, 3.5 h, 80% (2 steps)
intermediate structure
CrO3
Pyr
RT, 14 h, 93%
See the Sarett Oxidation
intermediate structure
MeI, KOt-Bu
PhH, t-BuOH
Reflux, 10 min, 24% (63% BRSM)
intermediate structure
NH2NH2, Na
Diethylene glycol
RT to 255 °C, 5.5 h, 71%
See the Wolff-Kishner Reduction
"The enantiomers were resolved with di-p-toluoyl-L-tartaric acid."
intermediate structure
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