Synthesis of Diplamine

Structure of Diplamine

C20H13N3O2S

Principal investigator	Clayton H. Heathcock
Publication year	1994
Synthesis type	Total
Number of steps	20 (3 parts)
References	J. Org. Chem. 1994, 59, 3512.

Part 1 of 3

intermediate structure

HCl

MeOH

0 to 25 °C, 24 h, 99%

See the Fischer-Speier Esterification

intermediate structure

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Part 2 of 3

intermediate structure

AcOH, HNO3

H2O

0 to 20 °C, 10 min, 84%

intermediate structure

H2, Pd/C

3.1 atm

THF

RT, 2 h, 100%

intermediate structure

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Part 3 of 3

intermediate structure

+

intermediate structure

m-Xylene

160 °C, 83%

intermediate structure

H2SO4

H2O

75 °C, 30 min, 81%

See the Knorr Quinoline Synthesis

intermediate structure

POCl3

50 °C, 60 min, 94%

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AcOH, HNO3

H2O

25 °C, 10 min, 83%

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POCl3

CHCl3

0 °C to RT, 84%

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AcOH, HNO3

H2O

25 °C, 10 min, 79%

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AcCl, Pyr

CH2Cl2

0 °C, 1 h, 96%

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HI

Acetone, H2O

RT, 1 min

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CH2N2

Et2O, EtOAc

0 °C, 24 h

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K2CO3

H2O, MeOH, THF

RT, 24 h, 82% (3 steps)

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Pyr.SO3, Et3N

DMSO

RT, 20 min, 81%

See the Parikh-Doering Oxidation

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Pyr, H2NSO3H

EtOH

Reflux, 30 min, 83%

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BH3.THF, MeOH

THF

RT, 9 h

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Ac2O

EtOAc

RT, 75% (2 steps)

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(NH4)2Ce(NO3)6

H2O, MeCN

25 °C, 90 min, 73%

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Et3N, NaSMe

CHCl3

RT, 10 min, 51%

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Zn
(NH4)2Ce(NO3)6

AcOH, H2O

Reflux, 60 min, 37%

intermediate structure

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