1,2,3,4-Tetrahydroisoquinoline → 1-(3-bromophenoxy)-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol

HRID 1051447노트

반응식

HRID 1051447 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH2:6][CH:7]1[CH2:9][O:8]1.[CH2:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][NH:14]1.CC(=O)OCC>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH2:6][CH:7]([OH:8])[CH2:9][N:14]1[CH2:15][CH2:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13]1

참가 물질

5

반응물 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 8857Ethyl AcetateHCID 38653422-[(3-Bromophenoxy)methyl]oxirane

생성물 1

HCID 429098461-(3-bromophenoxy)-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol수율 78.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 2-((3-bromophenoxy)methyl)oxirane (1.5 g, 6.55 mmol) in MeOH (15 mL) were added 1,2,3,4-tetrahydroisoquinoline (1.0 g, 7.86 mmol) at 8° C. The mixture was refluxed for 16 h. TLC (PE: EA=2:1) showed that the reaction was completed and the mixture was concentrated to yield crude material which was purified using column chromatography on silica gel to give the desired compound (1.8 g, 78.3%) as colorless oil. LCMS (m/z): 362.1/363.1 [M+H]+/[M+2H]+

후처리

  1. temperatureThe mixture was refluxed for 16 h
  2. concentrationthe mixture was concentrated
  3. customto yield crude material which
  4. customwas purified

출처 및 근거

ORD 기록
ord-41aedf6ae56d46288f730b5b41e8aba6
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388173B2

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