Ethyl cyanoacetate → cis-Cyano-[4-(octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetic acid ethyl ester

HRID 1809108노트

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HRID 1809108 반응식
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:10])[CH2:7][C:8]#[N:9])[CH3:4].Br[C:12]1[S:16][CH:15]=[C:14]([C:17]([N:19]2[CH:28]3[CH:23]([CH2:24][CH2:25][CH2:26][CH2:27]3)[CH2:22][CH2:21][CH2:20]2)=[O:18])[CH:13]=1>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:3]([O:5][C:6](=[O:10])[CH:7]([C:8]#[N:9])[C:12]1[S:16][CH:15]=[C:14]([C:17]([N:19]2[C@@H:28]3[C@@H:23]([CH2:24][CH2:25][CH2:26][CH2:27]3)[CH2:22][CH2:21][CH2:20]2)=[O:18])[CH:13]=1)[CH3:4]

참가 물질

6

반응물 3

HCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 43424594(5-Bromo-thiophen-3-yl)-(octahydro-quinolin-1-yl)-methanone

생성물 1

HCID 86646715cis-Cyano-[4-(octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetic acid ethyl ester수율 55.3%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매2회

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온도
60 °C

실험 절차

Sodium hydride (60% dispersion in mineral oil; 400 mg) was added to a solution of ethylcyanoacetate (0.450 g) in THF (10 mL) and the mixture stirred for 10 minutes. A solution of (5-bromo-thiophen-3-yl)-(octahydro-quinolin-1-yl)-methanone (0.326 g) and PdCl2(PPh3)2 (0.035 g) in THF (2 mL) was then added dropwise and the mixture heated to 60° C. overnight. The solvent was evaporated and the residue purified by flash chromatography on silica, washing with cyclohexane and ethyl acetate. The fractions containing the desired product were concentrated under vacuum to give the title compound as a clear oil (0.198 g). LCMS m/z 361.27 [M+H]+ RT=3.80 min (Analytical Method 3).

후처리

  1. customThe solvent was evaporated
  2. customthe residue purified by flash chromatography on silica
  3. washwashing with cyclohexane and ethyl acetate
  4. additionThe fractions containing the desired product
  5. concentrationwere concentrated under vacuum

출처 및 근거

ORD 기록
ord-62d9ceb81eeb411caac16488efe70c9d
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362008B2

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