2014/03/15-1 Medicinal Chemistry Route OH O 1) Rh/Al2O3, H2 MeO2C O 2) DIBAL-H 2) (COCl)2, DMSO, Et3N CO2Me O BnNH2 Na(OAc)3BH O 1) HO(CH2)2OH, p-TsOH O MeO2C CO2Me O 1) Pd/C, NH4CO2H EtOH; (Boc)2O OTf KHMDS Tf2NPh 2) acetone, p-TsOH OHC CHO N Boc N Bn Suzuki-Miyaura Cross Coupling O BPD, Pd(OAc)2, dppf B O N N 1) bromopyridine, Pd(dppf)2Cl2 K2CO3, DMF KOAc, dioxane N Boc CH2O, HCO2H 2) TFA N N Boc N Boc Process Route CHO (CH2O)n BF3·OEt2 O 1) NH2OH·HCl ClCO2Et NH2 N H 2) LiAlH4 H Br OEt CH2Cl2 Br Br Br KOt-Bu Br2 H2C N N N EtO EtO N B(OH)2 O O EtO N EtO O CH2O, HCO2H Eschweiler-Clarke Methylation N EtO EtO N c. HCl Suzuki-Miyaura Cross Coupling O N Pd(OAc)2, dppf N N O N H N O
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