Sodium ethoxide → (3R,4R)-1-tert-butyl 3-ethyl 4-((R)-1-phenylethylamino)-piperidine-1,3-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 252C (2.90 g, 7.71 mmol) in ethanol (70 mL) was treated with 21% NaOEt in ethanol (7.5 mL). The reaction mixture was heated to 50° C. for three hours, cooled to room temperature, and then concentrated. The resulting oil was taken up in dichloromethane (150 mL), washed with 20% NH4Cl (2×50 mL). The organic layer was dried (Na2SO4) and concentrated to an oil. Purification by flash chromatography (10 to 25% EtOAc/Hexane gradient) on silica gel afforded 1.20 g (yield: 41%) of Compound 252D as an oil.

Provenance & Evidence