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Hydrogen Peroxide → 1-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-5-(2-hydroxyethyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2-chloro-6-fluorophenyl)ethan-1-one

HRID 1854574
ノート
印刷プレビュー

反応式

HRID 1854574 の反応式
[Si:1]([O:8][CH2:9][C@H:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH:20]=[CH2:21])[C@H:12]([CH3:22])[N:11]1[C:23](=[O:33])[CH2:24][C:25]1[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:32])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-:34].[Na+].OO>C1COCC1>[Si:1]([O:8][CH2:9][C@H:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:20][CH2:21][OH:34])[C@H:12]([CH3:22])[N:11]1[C:23](=[O:33])[CH2:24][C:25]1[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:32])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 1235332471-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-5-vinyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2-chloro-6-fluorophenyl)ethan-1-one

生成物 1

HCID 1239773771-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-5-(2-hydroxyethyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2-chloro-6-fluorophenyl)ethan-1-one

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

反応条件

温度
0 °C

実験手順

Dissolve 1-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-5-vinyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2-chloro-6-fluorophenyl)ethan-1-one (1.54 g, 3.15 mmol) in THF (31 mL). Cool to 0° C. Add BH3 (6.3 mL, 6.3 mmol, 1M in THF). Stir 4 h at room temperature. Cool to 0° C. Add NaOH (12.6 mL, 3 M in water) and H2O2 (1.92 mL, 30% wt/wt % in water). Stir overnight at room temperature. Add ethyl acetate, wash with saturated NaHCO3 solution and brine, dry over sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue by silica gel chromatography, eluting with ethyl acetate: hexanes (gradient, 5-60%) to give 1-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-5-(2-hydroxyethyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2-chloro-6-fluorophenyl)ethan-1-one as a white foam (1.08 g, 2.13 mmol). MS (m/z): 506.2 (M+1).

後処理

  1. additionAdd
  2. temperatureCool to 0° C
  3. stirringStir overnight at room temperature
  4. washAdd ethyl acetate, wash with saturated NaHCO3 solution and brine
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customto give a residue
  9. customPurify the residue by silica gel chromatography
  10. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-4426d8915149450782d1613b6047351a
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08962654B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート