Cocaine for tropinone

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 Tropane Alkaloids || A Review

Synthesis of ecgonine & its derivatives

Contents
1. 1 Ecgonine
1. 1.1 2-Carbomethoxytropinone
2. 1.2 Cocaine
3. 1.3 Cocaethylene
Ecgonine
1. Ecgonine can be prepared from 2-carbomethoxytropinone, first by
reducing it, then hydrolysis.

2. Tropinone can be used as a starting material for ecgonine

synthesis.
R. Willsttter and W. Mller, Ber. Dtsch. Chem. Ges., 1898, 31, 2655
 2-Carbomethoxytropinone

01. Cyclization of 1-methyl-2,5-dicarboethoxypyrrolidine gives 2-

Carbomethoxytropinone.
R. Willstatter and M. Bommer, Ann., 422, 15 (1921)
R. Willstiitter and A. Pfannenstiehl, Ann., 422, 1 (1921)

02. 2-Carbomethoxytropinone can be obtained from modified

Robinson synthesis. (yield 20%).
German Patent 345,759

03. 2-Carbomethoxytropinone can be produced from Tropinone and

carbon dioxide in presence of sodium (or potassium) in benzene (or
xylene). Practically dimethyl carbonate is used as a source of carbon
dioxide. (yield 70-80%).
N. A. Preobrashenski, M. N. Schtschukina, and R. A. Lapina, Ber., 69,1615 (1936)
04. Willstatter's synthesis proceeds using dipotassium salt of
monomethyl beta-ketoglutarate.
R. Willstatter, 0. Wolfes, and H. Miider, Ann., 434, 111 (1923)

05. 2-Carbomethoxytropinone is obtained at a high yield from

modified Robinson synthesis.

06. Variation of Willstatter's synthesis using monomethyl beta-

ketoglutarate also yields 2-carbomethoxytropinone in satisfactory
quantity.
R. Willstiitter and A. Pfannenstiehl, Ann., 422, 1 (1921)
R. Kaushall, J. Indian Chem. SOL, 17,138 (1940)
 Cocaine

01. Willstters Preparation

Cocaine was first prepared in 1923 by Willstter. This synthesis

is very remarkable because, although at this time both the
relative and the absolute stereochemistry of cocaine were
unknown, they were able to prepare this alkaloid in optically
active form.
WILLSTTTER, R.; WOLFES, O.; MDER, H. Annalen 1923, 434, 111

02. Preobrazhenskiis Preparation

In 1958 a group of Soviet chemists made improvements

to Willstter's synthesis by the in situ generation of the unstable
butandial by acidic hydrolysis of dimethoxytetrahydrofuran.

BAZILEVSKAYA, G.I.; BAINOVA, M.S.; GURA, D.V.; DYUMAEV, K.M.; PREOBRAZHENSKII, N.A.
Isvest.Vysshikh.Ucheb.Zavedenii, Khim. i Khim.Tekhnol. 1958, 2, 75-81 (Chem.Abstr. 1959, 53, 423h).

BAINOVA, M.S.; BAZILEVSKAYA, G.I.; DYUMAEV, K.M.; PREOBRAZHENSKII,

N.A. Zh.Obshch.Khim. 1960, 30, 1120-1123 (Chem.Abstr.1961, 55, 530f)

BAINOVA, M.S.; BAZILEVSKAYA, G.I.; PREOBRAZHENSKII, N.A.

Zh.Obshch.Khim. 1960, 30, 3258-3261 (Chem.Abstr. 1961, 55, 21155d)

02. Tufariello synthesis using nitrone

TUFARIELLO, J.J.; TEGELER, J.J.; WONG, S.C.; ALI, S.A. Tetrahedron Lett. 1978, 30, 1733-1736

TUFARIELLO, J.J.; MULLEN, G.B.; TEGELER, J.J.; TRYBULSKI, E.J.; WONG, S.C.; ALI, S.A.
 J.Am.Chem.Soc. 1979, 101, 2435-2442

04. Carrolls Preparation

LEWIN, A.H.; NASEREE, T.; CAROLL, F.I. J.Heterocycl.Chem. 1987, 24, 19-21

CARROLL, F.I.; COLEMAN, M.L.; LEWIN, A.H. J.Org.Chem. 1982, 47, 13-19

05. Rapoports Preparation

LIN, R.; CASTELLS, J.; RAPOPORT, H. J.Org.Chem. 1998, 63, 4069-4078

PETERSEN, J.S.; FELS, G.; RAPOPORT, H. J.Am.Chem.Soc. 1984, 106, 4539-4547

06. Chas Preparation

LEE, J.C.; LEE, K.; CHA, J.K. J.Org.Chem. 2000, 65, 4773-4775

03. Pearson synthesis

Cocaethylene

01. Cocaethylene can be prepared from cocaine and ethanol by an

ester exchange reaction.

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