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

HRID 1051447ノート

反応式

HRID 1051447 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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]+

後処理

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

出典と根拠

ORDレコード
ord-41aedf6ae56d46288f730b5b41e8aba6
出典データセット
uspto-grants-2016_07
特許番号
US09388173B2

反応ノート

読み込み中…