Synthesis of Clavizepine

Structure of Clavizepine

C19H21NO4

Principal investigatorHiroyuki Ishibashi
Publication year1994
Synthesis typeTotal
Number of steps 15 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
SnCl4
CH2Cl2
RT, 30 min, 98%
intermediate structure
Zn
AcOH
Reflux, 5 h, 96%
intermediate structure + intermediate structure
CuO, K2CO3
Pyr
Reflux, 20 h, 61%
intermediate structure
  1. i-Pr2NLi
  2. O2
THF, HMPA
-78 °C to RT, 2 h, 63%
intermediate structure
SnCl4
CH2Cl2
0 °C to RT, 7 h, 66%
intermediate structure
H2, Pd/C
MeOH
RT, 7 d, 86%
intermediate structure
BnBr, K2CO3
Acetone
Reflux, 2 h, 92%
intermediate structure
MeNH2
MeOH
95 °C, 5 h, 92%
intermediate structure
BH3.THF
THF
Reflux, 10 d
intermediate structure + intermediate structure
Et3N
CH2Cl2
0 °C to RT, 9 h, 97% (2 steps)
intermediate structure
NaIO4
MeOH, H2O
0 °C to RT, 2.5 d
""Excellent yield""
intermediate structure
(CF3CO)2O
CH2Cl2
0 °C to RT, 2.5 d, 95%
intermediate structure
Zn
AcOH
Reflux, 5 h, 92%
intermediate structure
Red-Al
PhH
Reflux, 26 h, 62%
intermediate structure
Ni (Raney)
EtOH
Reflux, 5 h, 93%
intermediate structure