Lithium Chloride → cis-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetonitrile

HRID 1809109노트

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HRID 1809109 반응식
C(OC(=O)[CH:5]([C:23]#[N:24])[C:6]1[S:7][CH:8]=[C:9]([C:11]([N:13]2[C@@H:22]3[C@@H:17]([CH2:18][CH2:19][CH2:20][CH2:21]3)[CH2:16][CH2:15][CH2:14]2)=[O:12])[CH:10]=1)C.[Cl-].[Li+]>CS(C)=O.C(Cl)Cl>[N:13]1([C:11]([C:9]2[CH:10]=[C:6]([CH2:5][C:23]#[N:24])[S:7][CH:8]=2)=[O:12])[C@@H:22]2[C@@H:17]([CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:16][CH2:15][CH2:14]1

참가 물질

5

반응물 2

HCID 433294Lithium ChlorideHCID 86646715cis-Cyano-[4-(octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetic acid ethyl ester

생성물 1

HCID 86646716cis-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetonitrile수율 18.8%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매

반응 조건

온도
160 °C

실험 절차

cis-Cyano-[4-(octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetic acid ethyl ester (0.168 g, 0.46 mmol) and lithium chloride (0.5 mmol) were dissolved in DMSO (5 mL) and heated to 160° C. by microwave irradiation for one minute. The solution was diluted with DCM (10 mL) and washed with water. The resulting organic solution was dried and the solvent evaporated to give an oil which was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound as a colourless oil (0.025 g). LCMS m/z 289.25 [M+H]+ RT=10.02 min (Analytical Method 2).

후처리

  1. washwashed with water
  2. customThe resulting organic solution was dried
  3. customthe solvent evaporated
  4. customto give an oil which
  5. customwas purified by HPLC
  6. washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

출처 및 근거

ORD 기록
ord-24a3398ea6a74b27a0e159e900b36397
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362008B2

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