tert-Butylsulfinamide, (R)-(+)- → (NE,R)-2-methyl-N-[[4-(trifluoromethyl)pyridin-2-yl]methylidene]propane-2-sulfinamide

HRID 246013ノート

反応式

HRID 246013 の反応式
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]=O)[CH:4]=1.[CH3:13][C:14]([S@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][N:6]=[C:5](/[CH:9]=[N:19]/[S@@:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])[CH:4]=1

参加物

5

反応物 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 147614714-(Trifluoromethyl)pyridine-2-carbaldehyde

生成物 1

HCID 89421022(NE,R)-2-methyl-N-[[4-(trifluoromethyl)pyridin-2-yl]methylidene]propane-2-sulfinamide収率 75%

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-trifluoromethyl-pyridine-2-carbaldehyde (287 mg, 1.64 mmol) and (R)-2-methylpropane-2-sulfinamide (209 mg, 1.72 mmol) in CH2Cl2 (10 mL) was added anhydrous copper (II) sulfate (576 mg, 3.61 mmol). The reaction mixture was stirred at room temperature overnight then filtered over a Buchner funnel, rinsing with CH2Cl2. The filtrate was concentrated and the residue was absorbed on SiO2 and purified by chromatography with 20% to 40% EtOAc/hexanes to give 340 mg (75%) of (R)-2-methyl-propane-2-sulfinic acid 1-(4-trifluoromethyl-pyridin-2-yl)-meth-(E)-ylideneamide as a pale yellow oil.

後処理

  1. filtrationthen filtered over a Buchner funnel
  2. washrinsing with CH2Cl2
  3. concentrationThe filtrate was concentrated
  4. customthe residue was absorbed on SiO2
  5. custompurified by chromatography with 20% to 40% EtOAc/hexanes

出典と根拠

ORDレコード
ord-c960ddb87f50420680bd3681b19fc4a1
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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