Methyl 5-(3-((tert-butoxycarbonyl)amino)prop-1-yn-1-yl)furan-2-carboxylate → 5-(3-Tert-butoxycarbonylaminopropyl)-furan-2-carboxylic acid methyl ester

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Reaction Steps

To a solution of 5-(3-tert-butoxycarbonylamino-prop-1-ynyl)-furan-2-carboxylic Acid methyl ester (1.69 g) in MeOH (50 mL) was added 10% palladium on carbon (850 mg) and the mixture was hydrogenated on a Parr shaker at 50 psi for 18 h. The catalyst was removed via filtration through Celite and the volatiles were concentrated in vacuo. Flash chromatography (hexanes:EtOAc 4:1) provided 5-(3-tert-butoxycarbonylaminopropyl)-furan-2-carboxylic Acid methyl ester (422 mg, MS 284 M+) followed by 5-(3-tert-butoxycarbonylamino-propyl)-tetrahydrofuran-2-carboxylic Acid methyl ester (903 mg).

Provenance & Evidence