benzyl (S)-2-((R)-3-((S)-1-(benzofuran-7-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxamido)-3-cyclopentylpropylmethylcarbamate → (3R)-N-((S)-3-cyclopentyl-1-(methylamino)propan-2-yl)-3-((S)-1-(2,3-dihydrobenzofuran-7-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxamide

Participants

Reaction Steps

To a solution of benzyl (S)-2-((R)-3-((S)-1-(benzofuran-7-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxamido)-3-cyclopentylpropylmethylcarbamate (98.5 mg, 0.156 mmol) in EtOAc (10 mL) was added PdCl2 (30 mg) and the mixture was stirred under a hydrogen balloon at rt for 3˜5 hrs. After filtration, the filtrate was evaporated and the residue, was purified by prep HPLC to afford (3R)—N—((S)-3-cyclopentyl-1-(methylamino)propan-2-yl)-3-((S)-1-(2,3-dihydrobenzofuran-7-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxamide (36.2 mg, 46.5%). 1H NMR (CD3OD, 400 MHz) δ 0.89 (m, 1H), 1.12-2.15 (m, H), 2.58 (m, 2H), 2.71 (s, 3H), 2.93 (m, 1H), 3.15 (m, 3H), 3.23 (s, 3H), 3.98 (m, 2H), 4.26 (m, 1H), 4.48 (m, 2H), 6.83 (m, 1H), 7.12 (m, 1H), 7.21 (m, 1H).

Provenance & Evidence