Synthesis of Hyrtiazepine

Structure of Hyrtiazepine

C20H15N3O4

Principal investigator	Kentaro Yamaguchi
Publication year	2011
Synthesis type	Total
Number of steps	14 (3 parts)
References	Tetrahedron 2011, 67, 1805.

Part 1 of 3

intermediate structure

NaH, TsCl

THF

RT, 3 h, 94%

intermediate structure

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Part 2 of 3

intermediate structure

Imidazole, TBSCl

DMF

RT, 30 min

intermediate structure

NaH, TsCl

THF

RT, 2 h

intermediate structure

HCl

H2O, THF

Reflux, 2 h, 78 % (3 steps)

intermediate structure

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Part 3 of 3

intermediate structure

+

intermediate structure

PhB(OH)2, EtCO2H

Dean-Stark

PhMe

Reflux, 24 h, 77%

intermediate structure

MeI, K2CO3

DMF

RT, 2 h, 75%

intermediate structure

IBX

DMSO

RT, 2 h, 86%

intermediate structure

KOH

MeOH, THF

Reflux, 2 h, 86%

intermediate structure

TsCl, Et3N

CH2Cl2

RT, 7 h, 85%

intermediate structure

Special reagent

Ac2O

AcOH

80 °C, 3 h, 68%

intermediate structure

EtI, K2CO3

DMF

RT, 2 h, 82%

intermediate structure

HCl

EtOH, H2O

Reflux, 20 h, 70%

intermediate structure

BBr3

CH2Cl2

Reflux, 2 h, 80%

intermediate structure

K2CO3

MeOH

Reflux, 3 h, 65%

intermediate structure

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