Synthesis of Clavizepine

Structure of Clavizepine

C19H21NO4

Principal investigatorHiroyuki Ishibashi
Publication year1994
Synthesis typeTotal
Number of steps 15 (linear)
References
Tetrahedron 1994, 50, 10215.
Part 1 of 1
intermediate structure + intermediate structure
SnCl4
CH2Cl2
RT, 30 min, 98%
See the Friedel-Crafts Alkylation
intermediate structure
Zn
AcOH
Reflux, 5 h, 96%
intermediate structure + intermediate structure
CuO, K2CO3
Pyr
Reflux, 20 h, 61%
See the Ullmann Condensation
intermediate structure
  1. i-Pr2NLi
  2. O2
HMPA, THF
-78 °C to RT, 2 h, 63%
intermediate structure
SnCl4
CH2Cl2
0 °C to RT, 7 h, 66%
See the Bradsher Cyclization
intermediate structure
Pd/C, H2
6 atm
MeOH
RT, 7 d, 86%
intermediate structure
K2CO3, BnBr
Acetone
Reflux, 2 h, 92%
See the Williamson Ether Synthesis
intermediate structure
MeNH2
Sealed tube
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
H2O, MeOH
0 °C to RT, 2.5 d
""Excellent yield""
intermediate structure
(CF3CO)2O
CH2Cl2
0 °C to RT, 2.5 d, 95%
See the Pummerer Rearrangement
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
Report an error in this part