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6-(2,2-Dibromo-vinyl)-2-cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-6-carboxaldehyde → 2-Cyclopropyl-6-ethynyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline

HRID 24079
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인쇄 미리보기

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HRID 24079 반응식
Br[C:2](Br)=[CH:3][C:4]1(C=O)[CH:13]=[CH:12][C:11]2[CH2:10][N:9]([CH:14]3[CH2:16][CH2:15]3)[CH2:8][C:7]([CH3:18])([CH3:17])[C:6]=2[CH2:5]1.C([Li])CCC>O1CCCC1>[CH:14]1([N:9]2[CH2:8][C:7]([CH3:17])([CH3:18])[C:6]3[C:11](=[CH:12][CH:13]=[C:4]([C:3]#[CH:2])[CH:5]=3)[CH2:10]2)[CH2:16][CH2:15]1
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참가 물질

4

반응물 2

HCID 225688196-(2,2-Dibromo-vinyl)-2-cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-6-carboxaldehyde2회HCID 178418339Butyllithium

생성물 1

HCID 225689952-Cyclopropyl-6-ethynyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline수율 94.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-20 °C

실험 절차

A stirred, cooled (−78° C.) solution of 6-(2,2-dibromo-vinyl)-2-cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-6-carboxaldehyde (Intermediate 26, 0.1 8 g, 0.47 mmol) in tetrahydrofuran (2 mL) was treated with 1.6M solution of n-butyl lithium (0.6 mL, 0.96 mmol) under argon. The reaction mixture was allowed to warm to −20° C. over 1.5 h, quenched with saturated aqueous ammonium chloride solution and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound as an oil (0.1 g, 94%).

후처리

  1. customquenched with saturated aqueous ammonium chloride solution
  2. extractionextracted with diethyl ether (×2)
  3. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-58e55d59df9f4a95a6625f46f5b6e523
출처 데이터셋
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06855512B2

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