Synthesis of Diplamine

C20H13N3O2S
Principal investigator | Clayton H. Heathcock |
---|---|
Publication year | 1994 |
Synthesis type | Total |
Number of steps | 20 (3 parts) |
References |
Part 1 of 3
Part 2 of 3

AcOH,
HNO3
H2O
0 to 20 °C, 10 min, 84%

H2,
Pd/C
3.1 atm
THF
RT, 2 h, 100%

Part 3 of 3
+


m-Xylene
160 °C, 83%


POCl3
50 °C, 60 min, 94%

AcOH,
HNO3
H2O
25 °C, 10 min, 83%

POCl3
CHCl3
0 °C to RT, 84%

AcOH,
HNO3
H2O
25 °C, 10 min, 79%

AcCl,
Pyr
CH2Cl2
0 °C, 1 h, 96%

HI
Acetone, H2O
RT, 1 min

CH2N2
Et2O, EtOAc
0 °C, 24 h

K2CO3
H2O, MeOH, THF
RT, 24 h, 82% (3 steps)


Pyr,
H2NSO3H
EtOH
Reflux, 30 min, 83%

BH3.THF,
MeOH
THF
RT, 9 h

Ac2O
EtOAc
RT, 75% (2 steps)

(NH4)2Ce(NO3)6
H2O, MeCN
25 °C, 90 min, 73%

Et3N,
NaSMe
CHCl3
RT, 10 min, 51%

- Zn
- (NH4)2Ce(NO3)6
AcOH, H2O
Reflux, 60 min, 37%
