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

HRID 577440노트

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HRID 577440 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

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].

후처리

  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)

출처 및 근거

ORD 기록
ord-7c85c1f4d45d460c90f0da1e42c4f42f
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040515B2

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