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Trimethyl orthoformate → [4-(5-{[(Imidazol-2-ylmethyl)-amino]-methyl}-1-methoxyindan-2-yl)-butyl]-dipropylamine

HRID 348768
ノート
印刷プレビュー

反応式

HRID 348768 の反応式
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([O:12][CH3:13])[CH:7]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])[CH2:6]2.[NH:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH:30]=O.C(OC)(OC)OC.[BH4-].[Na+]>CO.O>[NH:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH2:30][NH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([O:12][CH3:13])[CH:7]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])[CH2:6]2
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 4311764Sodium borohydrideHCID 23079237[4-(5-Aminomethyl-1-methoxyindan-2-yl)-butyl]-dipropylamine

生成物 1

HCID 21084440[4-(5-{[(Imidazol-2-ylmethyl)-amino]-methyl}-1-methoxyindan-2-yl)-butyl]-dipropylamine収率 98.1%

試薬・触媒・溶媒 2

HCID 887
Methanol
溶媒
HCID 962Water溶媒

実験手順

The compound (45.0 mg) obtained in Example 127-13 was dissolved in methanol (2.25 ml) and added with 2-imidazole carboxaldehyde (19.5 mg) and trimethyl orthoformate (43.1 mg), followed by stirring at room temperature for 1 hour. Under ice-cooling, sodium borohydride (15.4 mg) was added to the solution, and the whole was stirred at room temperature for 30 minutes. The reaction solution was added with water and then subjected to separation/extraction with chloroform. The extract was washed with saturated saline solution, dried with anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (54.8 mg) as a yellow oily substance.

後処理

  1. temperatureUnder ice-cooling
  2. stirringthe whole was stirred at room temperature for 30 minutes
  3. extractionsubjected to separation/extraction with chloroform
  4. washThe extract was washed with saturated saline solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

出典と根拠

ORDレコード
ord-f949e1b3a06142658c54a371459885d0
出典データセット
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07176227B2

反応ノート

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