tert-Butylsulfinamide, (R)-(+)- → (R)-2-methyl-N-((4-(trifluoromethyl)pyridin-3-yl)methylene)propane-2-sulfinamide

HRID 509318ノート

反応式

HRID 509318 の反応式
[F:1][C:2]([F:12])([F:11])[C:3]1[C:8]([CH:9]=O)=[CH:7][N:6]=[CH:5][CH:4]=1.[CH3:13][C:14]([S@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>S([O-])([O-])(=O)=O.[Cu+2].C(Cl)Cl>[CH3:13][C:14]([S@:17]([N:19]=[CH:9][C:8]1[CH:7]=[N:6][CH:5]=[CH:4][C:3]=1[C:2]([F:12])([F:11])[F:1])=[O:18])([CH3:16])[CH3:15]

参加物

5

反応物 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 213547244-(Trifluoromethyl)pyridine-3-carbaldehyde

生成物 1

HCID 71144309(R)-2-methyl-N-((4-(trifluoromethyl)pyridin-3-yl)methylene)propane-2-sulfinamide

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 6344Dichloromethane溶媒

実験手順

To a the solution of 4-(trifluoromethyl)nicotinaldehyde from above was added DCM (10 mL), (R)-2-methylpropane-2-sulfinamide (1.553 g, 12.81 mmol; See Table 1, footnote 1) (AK Scientific) and copper sulfate (4.09 g, 25.6 mmol) (Aldrich, anhydrous). The suspension was stirred at rt under N2 for 68 h. The suspension was then filtered through Celite® brand filter agent, and the solid was washed with DCM (2×20 mL). The filtrates were concentrated and purified by ISCO (40 g, SiO2, 10-50% EtOAc/hexane) to give (R)-2-methyl-N-((4-(trifluoromethyl)pyridin-3-yl)methylene)propane-2-sulfinamide as a light yellow oil.

後処理

  1. filtrationThe suspension was then filtered through Celite® brand
  2. filtrationfilter agent
  3. washthe solid was washed with DCM (2×20 mL)
  4. concentrationThe filtrates were concentrated
  5. custompurified by ISCO (40 g, SiO2, 10-50% EtOAc/hexane)

出典と根拠

ORDレコード
ord-087e696d57264f4c89596413471a6c0c
出典データセット
uspto-grants-2015_08
特許番号
US09096527B2

反応ノート

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