Synthesis of Nupharamine

Structure of Nupharamine

C15H25NO2

Principal investigatorJosé Barluenga
Publication year1999
Synthesis typeTotal
Number of steps 12 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
ZnCl2
THF
-80 °C to RT, 16 h, 51%
intermediate structure
Triphosgene, Et3N
THF
0 °C, 15 min, 95%
intermediate structure
  1. TMS2NLi
  2. Comins' reagent
THF
-80 °C, 3 h, 67%
"The yield was 96 % brsm."
intermediate structure
H2, PtO2
EtOH
RT, 6-8 h, 89%
intermediate structure
KOt-Bu
THF
0 °C, 30 min, 95%
intermediate structure
TBSCl, Imidazole
MeCN
RT, 4 h, 67%
intermediate structure
ClCO2Bn, K2CO3
MeCN
RT, 4 h, 99%
intermediate structure
HCl
THF, H2O
RT, 30 min, 88%
intermediate structure + intermediate structure
  1. (COCl)2
  2. DMSO
  3. Et3N
  4. Ph3P=CHCO2Et
CH2Cl2
-65 °C to RT, 5 h
See the Swern Oxidation
See the Wittig Reaction
intermediate structure
H2, Pd/C
EtOH
RT, 3.5 h, 85%
intermediate structure
MeLi
THF
-70 °C, 15 min, 77%
intermediate structure
Pd, HCO2NH4
MeOH
RT, 14 h, 99%
intermediate structure