Synthesis of Quinine
C20H24N2O2
Principal investigator | Gilbert Stork |
---|---|
Publication year | 2001 |
Synthesis type | Total |
Number of steps | 17 (linear) |
References |
Part 1 of 1
+
+
AlMe3,
Et2NH
CH2Cl2
0 °C to RT, ON, 82%
Imidazole,
TBSCl
CH2Cl2
RT, 18 h, 97%
i-Pr2NLi
THF
-78 °C to RT, 5 h, 79%
Pyr.TsOH
EtOH
RT, ON, 93%
Xylene(s)
Reflux, 12 h, 97%
i-Bu2AlH
THF
-78 °C, 5 h
HCl
CH2Cl2, H2O, THF
RT, 8 h, 78%
i-Pr2NLi
THF
-78 to 0 °C, 65 min, 72%
NaBH4
MeOH, THF
RT, 3 h, 91%
HF
H2O, MeCN
RT, 60 min, 95%
MsCl,
Pyr
CH2Cl2
RT, ON
MeCN
Reflux, 3 h, 68% (2 steps)
NaH,
O2
DMSO
70 °C, 45 min, 78%