Synthesis of Quinine

C20H24N2O2

Principal investigator	Paul Rabe
Publication year	1918
Synthesis type	Partial
Number of steps	3 (linear)
References	Chem. Ber. 1918, 51, 466. Angew. Chem. Int. Ed. 2008, 47, 1736.

Part 1 of 1

HCl, NaOBr

Et2O, H2O

RT, 24 h, 55%

"The starting material (quinotoxine) was obtained from the degradation of natural quinine."

NaOEt

EtOH

Reflux, 10 min, 88%

See the Hofmann-Löffler-Freytag Reaction

Al, 																	
																						NaOEt

																	EtOH															

								Reflux, 								2 h, 								5%
							
								See the Meerwein-Ponndorf-Verley Reduction
							
								"(-)-Quinine was selectively cristallized (as a tartrate salt) from the resulting four diastereoisomers."

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