Synthesis of Hyrtiazepine

C20H15N3O4
Principal investigator | Kentaro Yamaguchi |
---|---|
Publication year | 2011 |
Synthesis type | Total |
Number of steps | 14 (3 parts) |
References |
Part 1 of 3

NaH,
TsCl
THF
RT, 3 h, 94%

Part 2 of 3

Imidazole,
TBSCl
DMF
RT, 30 min

NaH,
TsCl
THF
RT, 2 h

HCl
H2O, THF
Reflux, 2 h, 78 % (3 steps)

Part 3 of 3
+


PhB(OH)2,
EtCO2H
Dean-Stark
PhMe
Reflux, 24 h, 77%

MeI,
K2CO3
DMF
RT, 2 h, 75%

IBX
DMSO
RT, 2 h, 86%

KOH
MeOH, THF
Reflux, 2 h, 86%

TsCl,
Et3N
CH2Cl2
RT, 7 h, 85%


Ac2O
AcOH
80 °C, 3 h, 68%

EtI,
K2CO3
DMF
RT, 2 h, 82%

HCl
EtOH, H2O
Reflux, 20 h, 70%

BBr3
CH2Cl2
Reflux, 2 h, 80%

K2CO3
MeOH
Reflux, 3 h, 65%
