Hydrochloric Acid → HCID 53961705, compound

Participants

Reaction Steps

To a solution of 2-[4-(4-fluoro-benzyloxy)-benzenesulfonylamino]6-oxo-heptanoic acid tert-butyl ester (0.70 g, 1.5 mmol) in 6 mL of THF was added potassium tert-butoxide (0.7 mL of a 1M solution in THF, 0.70 mmol). After stirring for 24 h at room temperature, the mixture was diluted with water, acidified with 1M HCl and extracted 3× into ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Filtration of the residue through a pad of silica gel eluting with 1:1 ethyl acetate-hexane afforded 1-[4-(4-fluoro-benzyloxy)-benzenesulfonyl]-3-hydroxy-3-methyl-piperidine-2-carboxylic acid tert-butyl ester as a mixture of diastereomers. Separation of the diastereomers by radial chromatography (1-4% acetone-CH2Cl2, 4 mm plate) afforded 0.12 g of each diastereomer as a colorless oil.

Provenance & Evidence