Sodium bis(trimethylsilyl)amide → 3-((3S,6S)-6-Cyclohexyl-3-hydroxy-2-oxo-piperidin-1-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-((S)-2-cyclohexyl-6-oxo-piperidin-1-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (3.2 g, 7.97 mmol, 1.0 equiv) in THF (15.0 ml) was added NaHMDS (1.0 M in THF) at −78° C. and the resulting solution was stirred at −78° C. for 1.5 hours. To this solution was then added a solution of (S)-(+)-(camphorsulfonyl)oxaziridine (3.65 g, 15.94 mmol, 2.0 equiv) in THF (10 ml) and the reaction mixture was stirred at −78° C. for 3 hours. The reaction was quenched by addition of sat. NH4Cl aq. solution. The mixture was extracted with EtOAc and the combined organic layer was dried over Na2SO4, and concentrate. The residue was purified by silica gel column chromatography, (Et2O/DCM 5%˜40%) to give 1.5 g of the desired product (yield 45%). MS: 418 [M+H+]

Provenance & Evidence