Synthesis of Clavizepine

C19H21NO4
Principal investigator | Hiroyuki Ishibashi |
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Publication year | 1994 |
Synthesis type | Total |
Number of steps | 15 (linear) |
References |
Part 1 of 1
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Zn
AcOH
Reflux, 5 h, 96%



- i-Pr2NLi
- O2
HMPA, THF
-78 °C to RT, 2 h, 63%


Pd/C,
H2
6 atm
MeOH
RT, 7 d, 86%


MeNH2
Sealed tube
MeOH
95 °C, 5 h, 92%

BH3.THF
THF
Reflux, 10 d


Et3N
CH2Cl2
0 °C to RT, 9 h, 97% (2 steps)

NaIO4
H2O, MeOH
0 °C to RT, 2.5 d
""Excellent yield""


Zn
AcOH
Reflux, 5 h, 92%

Red-Al
PhH
Reflux, 26 h, 62%

Ni (Raney)
EtOH
Reflux, 5 h, 93%
