5-Propyl-2,3,6,7-tetrahydro-1H-azepine-2-carboxylic acid [2-chloro-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide → 5-Propyl-azepane-2-carboxylic acid [2-chloro-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide

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Reaction Steps

The unsaturated title compound from example 46 5-Propyl-2,3,6,7-tetrahydro-1H-azepine-2-carboxylic acid [2-chloro-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide (433 mg, 0.99 mmol) and 10% Pd/C (80 mg), were taken MeOH (10 mL) hydrogenated at 50 psi overnight. The solvent was removed to obtain the crude material. Purification was carried by silica gel column chromatography (20% MeOH/DCM) followed by preparative HPLC (general method AC) to furnish isomer 1 Rt=18.3 min (10 mg, 2.3%) and isomer 2 Rt=18.6 min (58 mg, 13.3%).

Provenance & Evidence