tert-Butylsulfinamide, (R)-(+)- → (NE,R)-2-methyl-N-[1-(5-methylsulfonylfuran-2-yl)propylidene]propane-2-sulfinamide

HRID 2198138ノート

反応式

HRID 2198138 の反応式
[CH3:1][S:2]([C:5]1[O:9][C:8]([C:10](=O)[CH2:11][CH3:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:14][C:15]([S@:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>C1COCC1.C(OCC)C.O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:1][S:2]([C:5]1[O:9][C:8](/[C:10](=[N:20]/[S@@:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19])/[CH2:11][CH3:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

参加物

7

反応物 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 592781411-(5-Methanesulfonyl-furan-2-yl)-propan-1-one

生成物 1

HCID 59278140(NE,R)-2-methyl-N-[1-(5-methylsulfonylfuran-2-yl)propylidene]propane-2-sulfinamide

試薬・触媒・溶媒 4

HCID 11026Titanium isopropoxide触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-(5-methanesulfonyl-furan-2-yl)-propan-1-one (1.1 g, 5.5 mmol) in THF (30 mL) was added (R)-(+)-2-methyl-2-propanesulfinamide (0.750 g, 6.06 mmol) and titanium (IV) isopropoxide (6 mL, 25 mmol) and the mixture was warmed at reflux. After 18 hours, the mixture was cooled to room temperature, and diluted with diethyl ether (100 mL) and water (6 mL). The mixture was stirred for 10 minutes, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography, eluting with a gradient of 0-80% EtOAc-hexanes to afford (R)-2-methyl-propane-2-sulfinic acid[1-(5-methanesulfonyl-furan-2-yl)-prop-(E)-ylidene]-amide.

後処理

  1. temperaturethe mixture was warmed
  2. temperatureat reflux
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of 0-80% EtOAc-hexanes

出典と根拠

ORDレコード
ord-f9ef314eb1ab4cabb92f4afe78d798ec
出典データセット
uspto-grants-2012_12
特許番号
US08338610B2

反応ノート

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