HCID 69332921, compound → HCID 178501287, compound

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Reaction Steps

A mixture of methyl 4-[1-tert-butoxycarbonyl-(2S)octahydroindolylmethoxy]benzoate (700 mg, 1.8 mmol) and 5% Rh on alumina (400 mg) in EtOH (10.0 ml) and AcOH (1.0 ml) was hydrogenated at room temperature at 5 atm for 48 hr. The catalyst was filtered off, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel with n-hexane-EtOAc (7:1, v/v) as eluent to give methyl cis-4-[1-tert-butoxycarbonyl-(2S)-octahydro indolylmethoxy]cyclohexanecarboxylate (600 mg, 85%) as a pale yellow oil. 1H-NMR (CDCl3) δ 1.10–2.35 (m, 20H), 1.44 (s, 9H), 3.45–3.90 (m, 5H), 3.80 (s, 3H).

Provenance & Evidence