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Cesium carbonate → cis-4-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-tetrahydro-pyran-4-carbonitrile

HRID 1809110
ノート
印刷プレビュー

反応式

HRID 1809110 の反応式
[N:1]1([C:11]([C:13]2[CH:14]=[C:15]([CH2:18][C:19]#[N:20])[S:16][CH:17]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.Br[CH2:22][CH2:23][O:24][CH2:25][CH2:26]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O.C(Cl)Cl>[N:1]1([C:11]([C:13]2[CH:14]=[C:15]([C:18]3([C:19]#[N:20])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[S:16][CH:17]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 21521Bis(2-bromoethyl) etherHCID 86646716cis-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetonitrile

生成物 1

HCID 86646717cis-4-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-tetrahydro-pyran-4-carbonitrile収率 32.8%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒
HCID 962
Water
溶媒
HCID 6344Dichloromethane溶媒

実験手順

cis-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetonitrile (0.049 g, 0.17 mmol) and 1-bromo-2-(2-bromo-ethoxy)-ethane (0.04 g, 0.17 mmol) and caesium carbonate (1.0 mmol) in DMSO (2 mL) was stirred for 12 hr at room temperature. The mixture was diluted with water (5 mL) and DCM (5 mL). The organic layer was filtered and then 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 (0.02 g). LCMS m/z 359.24 [M+H]+ RT=10.70 min (Analytical Method 2).

後処理

  1. filtrationThe organic layer was filtered
  2. customevaporated
  3. customto give an oil which
  4. customwas purified by HPLC
  5. washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
  6. additionThe fractions containing the desired product
  7. concentrationwere concentrated under vacuum

出典と根拠

ORDレコード
ord-d72f4e5fb04846bea7151a0e61ee5e1c
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08362008B2

反応ノート

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