Benzylethanolamine → HCID 178499151、化合物

HRID 1808347ノート

反応式

HRID 1808347 の反応式
[CH:1]([C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9])=O.[O-]S([O-])(=O)=O.[Na+].[Na+].[CH2:19]([NH:26][CH2:27][CH2:28][OH:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.O>[CH2:19]([N:26]([CH2:1][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9])[CH2:27][CH2:28][OH:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

8

反応物 5

HCID 4348BenzylethanolamineHCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 178499152Methyl 5-formyl-1H-imidazole-4-carboxylate

生成物 1

HCID 178499151HCID 178499151、化合物収率 99%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

Methyl 4-formyl-1H-imidazole-5-carboxylate (1.68 mmol, 1 equiv.) was taken up in dry THF (10 ml). Dry Na2SO4 (15.53 mmol, 9.2 equiv.) and N-benzylethanolamine (1.99 mmol, 1.18 equiv.) were added, and the mixture was stirred for 1 h at 25° C. under nitrogen. NaBH(OAc)3 (2.36 mmol, 1.4 equiv.) was then added in portions, and the reaction mixture was stirred for 16 h. Then water (5 ml) was added, and the mixture was neutralised with sat. NaHCO3 solution (10 ml). Extraction with DCM (2×20 ml) was carried out, and the combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The resulting crude product was purified by column chromatography (silica gel, 5-10% MeOH in DCM), and the desired product was thus obtained in the form of a white solid. Yield: 99%

後処理

  1. stirringthe reaction mixture was stirred for 16 h
  2. extractionExtraction with DCM (2×20 ml)
  3. dry with materialthe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude product was purified by column chromatography (silica gel, 5-10% MeOH in DCM)

出典と根拠

ORDレコード
ord-2199dc5a437048fbab7dbe0aa070d566
出典データセット
uspto-grants-2013_01
特許番号
US08357717B2

反応ノート

読み込み中…