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

HRID 246013노트

반응식

HRID 246013 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c960ddb87f50420680bd3681b19fc4a1
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

반응 노트

불러오는 중…