反応式
CON(C)[C:4](=[O:15])[CH:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:6].C(=O)=O.C(#N)C.C([Mg]Cl)(C)C.Br[Mg][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1>C1COCC1>[O:15]=[C:4]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)[C@@H:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH3:6]参加物
実験手順
tert-Butyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (50.0 g, 215 mmol) in THF (450 mL) was cooled to −40° C. (dry ice/acetonitrile) and slowly charged with isopropylmagnesium chloride (2.0M, 102.2 mL, 0.95 eq). After a clear solution was obtained (became clear at −20° C. and milky again at −40° C.), bromo(pyridin-2-ylmethyl)magnesium solution (see below for preparation) was added drop wise using cannula before warming to rt overnight. The reaction mixture was quenched with NH4Cl solution and extracted with EtOAc (500 mL×2). The combined organic layers were washed with water, brine, dried over sodium sulfate, and concentrated under high vacuum to give (S)-tert-butyl 3-oxo-4-(pyridin-2-yl)butan-2-ylcarbamate as a tan oil. Small scale reaction was purified by combiflash (EtOAc/hexane, up to 1/3) to give a red oil. Mass Spectrum (ESI) m/e=265 (M+1).
後処理
- customAfter a clear solution was obtained (
- custombecame clear at −20° C.
- customThe reaction mixture was quenched with NH4Cl solution
- extractionextracted with EtOAc (500 mL×2)
- washThe combined organic layers were washed with water, brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated under high vacuum
出典と根拠
- ORDレコード
- ord-6dfe5724be4149c79381fa186e91e7bf
- 出典データセット
- uspto-grants-2014_01
- 特許番号
- US08633313B2
関連ノート
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