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

HRID 1809109ノート

反応式

HRID 1809109 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
160 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-24a3398ea6a74b27a0e159e900b36397
出典データセット
uspto-grants-2013_01
特許番号
US08362008B2

反応ノート

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