Synthesis of Quinine

C20H24N2O2
Principal investigator | Gilbert Stork |
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Publication year | 2001 |
Synthesis type | Total |
Number of steps | 17 (linear) |
References |
Part 1 of 1
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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%
