3,7-Dibenzyl-3,7-diazabicyclo[3.3.1]nonan-9-one → HCID 22490261, compound

Participants

Reaction Steps

A solution of 3,7-dibenzyl-3,7-diazabicyclo[3.3.1]nonane-9-one (from step (i) above; 2.05 g; 6.4 mmol) in diethyl ether (15 mL) was added to a stirred solution of methyl magnesium chloride (12.8 mmol) in diethyl ether (8 mL) over 80 minutes. The reaction mixture was subsequently stirred for 20 minutes and then quenched with HCl (1 M). The aqueous layer was separated, concentrated and partitioned between EtOAc and NaOH (2 M). The organic layer was separated and subsequently treated with ion exchange resin (Amberlyst IRA 400), the solvent removed and the residue subjected to column chromatography (hexane:EtOAc; 1:1 with NH3 sat. MeOH; gradient 0-32%) to give the sub-tide compound as a diastereoisomeric mixture in a 60% yield.

Provenance & Evidence