Sodium borohydride → benzyl 4-((1R,2S)-2-{2-[(5-amino-3-methylpyridin-2-yl)oxy]ethyl}cyclopropyl)piperidine-1-carboxylate

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Reaction Steps

To the solution of NiCl2 (Nickel (II) Chloride-hexahydrate) in 12 ml of methanol was added 50 mg of NaBH4 (solution turned dark) at room temperature and the resulting mixture was stirred for 5 minutes. Benzyl 4-((1R,2S)-2-{2-[(3-methyl-5-nitropyridin-2-yl)oxy]ethyl}cyclopropyl)piperidine-1-carboxylate (from Step A; 550 mg, 1.25 mmol) in 5 ml of DCM was then added followed by the addition of 116 mg of NaBH4 in 3 portions. The mixture was then stirred for 20 minutes and then diluted with DCM and filtered through a pad of sodium sulfate (messy). The solution was concentrated to dryness under reduced pressure and taken up in 15 mL DCM. This material was then filtered through a pad of silica gel (extracting with ethyl acetate) and the filtrate was then washed by saturated aq. NaHCO3. The organics were then dried over sodium sulfate, filtered, and concentrated to dryness under reduced pressure to afford the title compound as a crude product which was used for next step. MS (ESI) m/z 410 [M+H]+.

Provenance & Evidence