Sodium hydride → 6-Chloro-3-(4-methoxy-benzyl)-7b-methyl-2-oxo-1,2,3,7b-tetrahydro-3-aza-cyclo-propa[a]naphthalene-1a-carboxylic acid ethyl ester

HRID 1745853노트

반응식

HRID 1745853 반응식
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH2:9]([O:11][C:12]([C:14]1[C:15](=[O:35])[N:16]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:17]2[C:22]([C:23]=1[CH3:24])=[CH:21][C:20]([Cl:25])=[CH:19][CH:18]=2)=[O:13])[CH3:10]>CS(C)=O>[CH2:9]([O:11][C:12]([C:14]12[CH2:24][C:23]1([CH3:4])[C:22]1[C:17]([N:16]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=3)[C:15]2=[O:35])=[CH:18][CH:19]=[C:20]([Cl:25])[CH:21]=1)=[O:13])[CH3:10]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 210202506-Chloro-1-(4-methoxy-benzyl)-4-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid ethyl ester

생성물 1

HCID 210202446-Chloro-3-(4-methoxy-benzyl)-7b-methyl-2-oxo-1,2,3,7b-tetrahydro-3-aza-cyclo-propa[a]naphthalene-1a-carboxylic acid ethyl ester수율 73.2%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
80 °C

실험 절차

A suspension of sodium hydride in anhydrous DMSO was treated in two portions with trimethylsulfoxonium iodide (0.33 g, 1.50 mmol). The reaction mixture was stirred for 30 min, treated with 3 (0.29 g, 0.752 mmol), and heated to 80° C. for 12 h. The resulting amber solution was allowed to cool to room temperature and poured over ice water. The milky suspension was extracted with CH2Cl2, dried (Na2SO4), filtered, and concentrated in vacuo. Chromatography provided 4 (0.22 g, 72%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.45 (d, J=2.3 Hz, 1H), 7.13 (d, J=8.6 Hz, 2H), 7.05 (dd, J=2.2, 9 Hz, 1H), 6.84 (d, J=8.6 Hz, 3H), 5.12 (m, 2H), 4.31 (m, 2H), 3.76 (s, 3H), 2.11 (d, J=6.6 Hz, 1H), 1.58 (s, 3H), 1.31 (t, J=7.2 Hz, 3H), 1.08 (d, J=6.6 Hz, 1H).

후처리

  1. temperatureto cool to room temperature
  2. extractionThe milky suspension was extracted with CH2Cl2
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a4a9867dbc794bc589808a29a24a84bd
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07019141B2

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