Synthesis of Nupharamine

Structure of Nupharamine

C15H25NO2

Principal investigator	Franklin A. Davis
Publication year	2006
Synthesis type	Formal
Number of steps	8 (linear)
References	J. Org. Chem. 2006, 71, 4222.

Part 1 of 1

intermediate structure

+

intermediate structure

Ti(OEt)4

CH2Cl2

RT, 5 h, 92%

intermediate structure

TMS2NK, 2-Butanone

Et2O

-78 °C, 90 min, 84%

See the Mannich Reaction

intermediate structure

CF3CO2H

MeOH

0 °C, 2 h

intermediate structure

+

intermediate structure

MgSO4

CH2Cl2

RT, 2 h, 86% (2 steps)

intermediate structure

TsOH

PhH

60 °C, 4 h, 74%

See the Mannich Reaction

intermediate structure

BF3.OEt2, (CH2SH)2

CH2Cl2

0 °C to RT, 2 h, 93%

intermediate structure

Ni (Raney)

EtOH

Reflux, 2 h, 78%

intermediate structure

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Remaining...

(3 steps)

"See: J. Org. Chem. 1999, 64, 3736."

intermediate structure