Synthesis of Diplamine

Structure of Diplamine

C20H13N3O2S

Principal investigatorClayton H. Heathcock
Publication year1994
Synthesis typeTotal
Number of steps 20 (3 parts)
References
Part 1 of 3
intermediate structure
HCl
MeOH
0 to 25 °C, 24 h, 99%
intermediate structure
Part 2 of 3
intermediate structure
AcOH, HNO3
H2O
0 to 20 °C, 10 min, 84%
intermediate structure
H2, Pd/C
3.1 atm
THF
RT, 2 h, 100%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
m-Xylene
160 °C, 83%
intermediate structure
H2SO4
H2O
75 °C, 30 min, 81%
intermediate structure
POCl3
50 °C, 60 min, 94%
intermediate structure
AcOH, HNO3
H2O
25 °C, 10 min, 83%
intermediate structure
POCl3
CHCl3
0 °C to RT, 84%
intermediate structure
AcOH, HNO3
H2O
25 °C, 10 min, 79%
intermediate structure
AcCl, Pyr
CH2Cl2
0 °C, 1 h, 96%
intermediate structure
HI
Acetone, H2O
RT, 1 min
intermediate structure
CH2N2
Et2O, EtOAc
0 °C, 24 h
intermediate structure
K2CO3
H2O, MeOH, THF
RT, 24 h, 82% (3 steps)
intermediate structure
Pyr.SO3, Et3N
DMSO
RT, 20 min, 81%
intermediate structure
Pyr, H2NSO3H
EtOH
Reflux, 30 min, 83%
intermediate structure
BH3.THF, MeOH
THF
RT, 9 h
intermediate structure
Ac2O
EtOAc
RT, 75% (2 steps)
intermediate structure
(NH4)2Ce(NO3)6
H2O, MeCN
25 °C, 90 min, 73%
intermediate structure
Et3N, NaSMe
CHCl3
RT, 10 min, 51%
intermediate structure
  1. Zn
  2. (NH4)2Ce(NO3)6
AcOH, H2O
Reflux, 60 min, 37%
intermediate structure