Sodium t-butoxide → (2S,3aR,7aS)-Ethyl 1-((S)-1-phenylethyl)octahydro-1H-indole-2-carboxylate

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Reaction Conditions

Reaction Steps

Tetrahydrofuran (210 mL) was charged to 1 L flask containing ethyl 2-(((1S,2S)-2-((methylsulfonyloxy)methyl)cyclohexyl)((S)-1-phenylethyl)amino)acetate (14, 30.1 g), sodium t-butoxide (9.6 g) was added at ambient temperature between 19-24° C. under nitrogen. The mixture was then heated to 65° C. and stirred for NLT 1 hour and cooled to 5° C. It was then quenched with a solution of ammonium chloride (10.69 g) in water (34 mL) and concentrated to about 100 mL volume. The mixture was diluted with heptanes (210 mL) and water (105 mL) and the aqueous layer is further extracted with heptanes (2×105 mL). The combined organic layers were washed with water (105 mL), followed by 3.5 M aqueous sodium chloride solution (105 mL). The heptane layer was dried with anhydrous sodium sulfate and concentrated under vacuum to afford 20.65 g of crude compound (15), which was purified on silica gel (700 g) chromatography using 3-4% ethyl acetate in hexanes to afford 8.24 g of (2S,3aR,7aS)-ethyl 1-((S)-1-phenylethyl)octahydro-1H-indole-2-carboxylate (15) as a viscous oil.

Provenance & Evidence