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

온도

-78 °C

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+]

1. stirringthe reaction mixture was stirred at −78° C. for 3 hours
2. customThe reaction was quenched by addition of sat. NH4Cl aq. solution
3. extractionThe mixture was extracted with EtOAc
4. dry with materialthe combined organic layer was dried over Na2SO4
5. concentrationconcentrate
6. customThe residue was purified by silica gel column chromatography, (Et2O/DCM 5%˜40%)

ORD 기록

ord-82dc0ee844dd4664bbdba16f1ac182fa

출처 데이터셋

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09040690B2