tert-Butyl piperazine-1-carboxylate → HCID 131736841, compound

Participants

Reaction Steps

A suspension of 4-(4-amino-5-((benzyloxy)methyl)-2-butyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl)butanal (268 mg, 0.704 mmol) and 4 Å molecular sieves in anhydrous dichloromethane (20 mL) was placed under nitrogen and tert-butyl piperazine-1-carboxylate (262 mg, 1.409 mmol) added. The reaction mixture was stirred at ambient temperature for 1 min then sodium triacetoxyborohydride (299 mg, 1.409 mmol) added and the reaction stirred for a further 30 min, Additional 4 Å molecular sieves were added and the reaction mixture stirred at ambient temperature for an additional 16.5 hours, The reaction mixture was filtered through celite and the cake washed with DCM. The solvent was removed in vacuo to give a viscous yellow oil. The oil was redissolved in DCM (50 mL). The organic layer was washed with saturated sodium hydrogen carbonate solution (50 mL), the layers separated and the aqueous layer back-extracted with DCM (2×25 mL). The combined organic phases were dried through a hydrophobic frit and concentrated in vacuo to give a yellow gum (488 mg). The sample was dissolved in dichloromethane and purified by chromatography on a silica cartridge (100 g) using a 0-10% MeOH:TBME gradient over 40 mins. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a pale yellow gum (338 mg).

Provenance & Evidence