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Trimethyl orthoformate → {4-[(4-dipropylamino-butylamino)-methyl]-benzyl}-carbamic Acid t-butyl Ester

HRID 348718
ノート
印刷プレビュー

反応式

HRID 348718 の反応式
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:18]([N:21]([CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])[CH2:19][CH3:20].C(OC)(OC)OC.[BH4-].[Na+]>CO.O>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:26][CH2:25][CH2:24][CH2:23][CH2:22][N:21]([CH2:27][CH2:28][CH3:29])[CH2:18][CH2:19][CH3:20])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]
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 2794832tert-Butyl hydrogen ((4-formylphenyl)methyl)carbonimidateHCID 4311764Sodium borohydrideHCID 7138396N,N-dipropylbutane-1,4-diamine

生成物 1

HCID 66941782{4-[(4-dipropylamino-butylamino)-methyl]-benzyl}-carbamic Acid t-butyl Ester収率 79.4%

試薬・触媒・溶媒 2

HCID 887
Methanol
溶媒
HCID 962Water溶媒

実験手順

The compound (225.3 mg) obtained in Example 103-3 was dissolved in methanol (6.76 ml). Then, the solution was added with the compound (165.0 mg) obtained in Example 1-2 and trimethyl orthoformate (304.8 mg), followed by stirring at room temperature for 18 hours. Sodium borohydride (108.7 mg) was added to the solution under ice-cooling, followed by stirring at room temperature for 0.5 hours. The reaction solution was added with water and subjected to separation/extraction with chloroform. Then, the extract was washed with saturated saline solution and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (297.6 mg) as a colorless oily substance.

後処理

  1. temperaturecooling
  2. stirringby stirring at room temperature for 0.5 hours
  3. extractionsubjected to separation/extraction with chloroform
  4. washThen, the extract was washed with saturated saline solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

出典と根拠

ORDレコード
ord-b0c60fc8ae274c659ebaab002b8736cf
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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