Chlorosuccinimide → Methyl 8-chloro-1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate

HRID 577440ノート

反応式

HRID 577440 の反応式
[O:1]=[C:2]1[C:11]2[CH:10]=[C:9]([O:12][CH:13]([CH3:15])[CH3:14])[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]=2[CH2:5][CH2:4][NH:3]1.C1C(=O)N([Cl:27])C(=O)C1>CC(O)=O>[Cl:27][C:10]1[C:11]2[C:2](=[O:1])[NH:3][CH2:4][CH2:5][C:6]=2[C:7]([C:16]([O:18][CH3:19])=[O:17])=[CH:8][C:9]=1[O:12][CH:13]([CH3:15])[CH3:14]

参加物

4

反応物 2

HCID 31398ChlorosuccinimideHCID 86723679Methyl 1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate

生成物 1

HCID 86723680Methyl 8-chloro-1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate収率 40%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

To a solution of methyl 1-oxo-7-(propan-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate (Cpd E, 400 mg, 1.52 mmol) in AcOH (5 mL) was added NCS (416 mg, 3.04 mmol). The reaction mixture was stirred at 100° C. overnight. The reaction mixture was concentrated under vacuum and the residue was diluted with H2O and NaHCO3 (sat., aq.). The aqueous layer was extracted with EtOAc and the organic layer purified by column chromatography (50% EtOAc/heptanes) to give the title compound (Cpd F, 180 mg, 40%) as a white solid. 1H NMR (400 MHz, chloroform-d) δ 1.40 (s, 3H) 1.42 (s, 3H) 3.27-3.36 (m, 2H) 3.37-3.47 (m, 2H) 3.88-3.95 (m, 3H) 4.62 (dt, J=12.07, 6.13 Hz, 1H) 6.06 (br. s., 1H) 7.61 (s, 1H); MS 298.0 [M+H].

後処理

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additionthe residue was diluted with H2O and NaHCO3 (sat., aq.)
  3. extractionThe aqueous layer was extracted with EtOAc
  4. customthe organic layer purified by column chromatography (50% EtOAc/heptanes)

出典と根拠

ORDレコード
ord-7c85c1f4d45d460c90f0da1e42c4f42f
出典データセット
uspto-grants-2015_05
特許番号
US09040515B2

反応ノート

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