Synthesis of Cocaine

Structure of Cocaine

C17H21NO4

Principal investigator	Joseph J. Tufariello
Publication year	1978
Synthesis type	Total
Number of steps	9 (linear)
References	J. Am. Chem. Soc. 1978, 100, 3638. J. Am. Chem. Soc. 1979, 101, 2435.

Part 1 of 1

intermediate structure

+

intermediate structure

HgO

PhMe

Reflux, 15 h, 96%

See the Huisgen Cycloaddition

intermediate structure

mCPBA

CH2Cl2

0 °C to RT, 2 h

intermediate structure

Methyl acrylate

PhMe

Reflux, 20 h, 77% (2 steps)

intermediate structure

MsCl

Pyr

0 °C to RT, 4 h, 95%

intermediate structure

DBN

PhH

RT, 4 h, 86%

intermediate structure

Xylene(s)

Reflux, 3 h

See the Huisgen Cycloaddition

intermediate structure

MeI

CH2Cl2, Et2O

RT, 12 h, 58%

intermediate structure

Zn

AcOH, H2O

70 °C, 3.5 h, 47%

intermediate structure

BzCl, Na2CO3

PhH

Reflux, 10 h, 37%

intermediate structure

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