tert-Butylsulfinamide, (R)-(+)- → (NE,R)-N-[1-(6-bromo-3-fluoro-4-triethylsilyl-2-pyridinyl)ethylidene]-2-methylpropane-2-sulfinamide

A mixture of titantetraethoxide (4.26 g, 18.69 mmol), (R)-tert.-butylsulfinamide (1.246 g, 10.28 mmol) and 1-(6-bromo-3-fluoro-4-triethylsilanyl-pyridin-2-yl)-ethanone (3.45 g, 9.34 mmol, 90% pure) in THF (25 ml) was refluxed under a nitrogen atmosphere for 6 hours. The cold reaction mixture was poured onto icecold brine (200 ml) with gentle stirring. The precipitate was filtered through a pad of hyflo and washed with ethyl acetate. The filtrate was diluted with ethyl acetate and washed with brine, dried over sodium sulfate, filtered and evaporated. The crude yellow oil (4.55 g) was chromatographed over silica gel (cyclohexane/ethyl acetate 94:6) to give the title compound as a yellow oil. 3.35 g (82% yield).

1. temperaturewas refluxed under a nitrogen atmosphere for 6 hours
2. customThe cold reaction mixture
3. filtrationThe precipitate was filtered through a pad of hyflo
4. washwashed with ethyl acetate
5. additionThe filtrate was diluted with ethyl acetate
6. washwashed with brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customevaporated
10. customThe crude yellow oil (4.55 g) was chromatographed over silica gel (cyclohexane/ethyl acetate 94:6)

ORDレコード

ord-ddc46a001ae649c3bb20d4adc22e1618

出典データセット

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09163011B2