Tert-butyl 3-oxopyrrolidine-1-carboxylate → Benzyl 4-(pyrrolidin-3-yl)piperazine-1-carboxylate

Participants

Reaction Steps

1-N-BOC-3-pyrrolidinone (500 mg, 2.70 mmol), benzyl-1-piperazinecarboxylate (595 mg, 2.70 mmol) and titanium (IV) isopropoxide (960 mg, 3.37 mmol) are stirred under argon for 1 hour. Ethanol (3 ml) and sodium cyanoborohydride (113 mg, 1.80 mmol) are added and the reaction mixture stirred at room temperature over night. The compound is purified by reverse phase column chromatography (Isolute™ C18, 0-100% MeCN in water—0.1% TFA), followed by deprotection using trifluoroacetic acid (5 ml). The solvent is removed in vacuo and the compound is partitioned between chloroform and saturated NaHCO3(aq). The organics are dried (MgSO4), filtered and reduced in vacuo to yield the title compound.

Provenance & Evidence