WO2010056717 Substituted bicyclic amines for the treatment of diabetes

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Scaffold: pyrrolidine-cyclopentane

Biological target:

Somatostatin receptor subtype 5: SSTR5



Steps Conditions Reactions
a EtI / K2CO3 / DMF Ethoxy synthesis
b 4-Fluorophenylboronic acid / Pd2(dba)3 / tri-t-butylphosphonium tetrafluoroborate / CsF / Dioxane Suzuki reaction
c LAH / THF Hydroxyl synthesis (Ester reduction)
d MsCl / Et3N / DCM Mesyl synthesis 
Steps Conditions Reactions
a thiophosgene / THF Cyclisation
b SOCl2 / DMF Chlorination
Steps Conditions Reactions
a Cbz-Cl / Et3N / DCM Cbz protection
b HCl 4N / Dioxane N-Boc deprotection
c Cs2CO3 / DMF Tertiary amine synthesis (nucleophilic substitution)
d H2 / Pd(OH)2 on carbon / MeOH  Cbz deprotection 
e Et3N / ACN Secondary amine synthesis (nucleophilic substitution)