Sodium Bicarbonate → 4-(3'-Fluoro-5'-hydroxymethyl-2,3,5,6-tetrahydro-[1,2']bipyridinyl-4-ylideneaminooxy)-piperidine-1-carboxylic acid isopropyl ester

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Reaction Steps

The crude 53b was taken up with methanol (10 mL), cooled in an ice bath and treated with NaBH4 (0.52 g, 13.7 mmol). The mixture was stirred for 2 h and treated with aqueous NaHCO3 (10 mL). The mixture was extracted with 40 mL of ethyl acetate, washed with brine (3×30 mL) and concentrated under vacuum. The residue was purified by flash chromatography (eluent: 20 to 70% ethyl acetate+0.1% triethylamine in hexane) to afford 296 mg (44% yield) of 53-1: LC-MS 409.2 (MH+), tR=5.59 (Method 2). EC50: 224 nM.

Provenance & Evidence