Imidazole → 2-(3-Bromo-2-((tert-butyldimethylsilyl)oxy)propyl)isoindoline-1,3-dione

HRID 624579ノート

反応式

HRID 624579 の反応式
[Br:1][CH2:2][CH:3]([OH:16])[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].N1C=CN=C1.[C:22]([Si:26](Cl)([CH3:28])[CH3:27])([CH3:25])([CH3:24])[CH3:23]>CN(C=O)C.CN(C1C=CN=CC=1)C.CCOC(C)=O>[Br:1][CH2:2][CH:3]([O:16][Si:26]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:28])[CH3:27])[CH2:4][N:5]1[C:6](=[O:15])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]1=[O:14]

参加物

7

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2220382-(3-Bromo-2-hydroxypropyl)-1h-isoindole-1,3(2h)-dione

生成物 1

HCID 867229042-(3-Bromo-2-((tert-butyldimethylsilyl)oxy)propyl)isoindoline-1,3-dione

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 2-(3-bromo-2-hydroxypropyl)isoindoline-1,3-dione (100 mg, 0.352 mmol) in DMF (0.5 mL) was added dropwise to a mixture of DMAP (43.0 mg, 0.352 mmol), imidazole (47.9 mg, 0.704 mmol) and tertbutyldimethylsilyl chloride (74.3 mg, 0.493 mmol) in DMF (1 mL). The mixture was stirred at room temperature for 18 hours. The mixture was diluted with EtOAc (20 ml) and washed with saturated NaHCO3(aq) (20 ml) and brine (3×10 ml). The organic phase was dried over magnesium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-100% EtOAc/hexane, afforded the title compound.

後処理

  1. washwashed with saturated NaHCO3(aq) (20 ml) and brine (3×10 ml)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customevaporated under vacuum
  4. customPurification by chromatography on silica
  5. washeluting with 0-100% EtOAc/hexane

出典と根拠

ORDレコード
ord-e45721bb52594e388b37666a6fc40acc
出典データセット
uspto-grants-2016_04
特許番号
US09303035B2

反応ノート

読み込み中…