Sodium borohydride → HCID 66582823, compound

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Reaction Steps

To a solution of racemic 9-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-9-azabicyclo[331]nonan-3-one (81 mg, 0.142 mmol, Example 140) in 1 mL of THF and 0.3 mL of MeOH was added sodium borohydride (10.72 mg, 0.284 mmol, Sigma-Aldrich, St. Louis, Mo.). The mixture was allowed to gradually warm to room temperature and stirred for 16 h. The crude material was then diluted with EtOAc (10 mL) and water (10 mL). The organic layer was separated and the extracts were washed with water (10 mL) and brine (10 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The crude material was by purified via reverse-phase preparative HPLC using a Phenomenex Gemini C18 column (150×30 mm, 10 μm) eluting with 0.1% TFA in CH3CN/H2O (5% to 100% over 15 min) to give 9-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-9-azabicyclo[3.3.1]nonan-3-ol (22 mg) as a mixture of two isomers:

Provenance & Evidence