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

HRID 348718
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 348718
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 9005Trimethyl orthoformateHCID 2794832tert-Butyl hydrogen ((4-formylphenyl)methyl)carbonimidateHCID 4311764Sodium borohydrideHCID 7138396N,N-dipropylbutane-1,4-diamine

Produkt 1

HCID 66941782{4-[(4-dipropylamino-butylamino)-methyl]-benzyl}-carbamic Acid t-butyl EsterAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-b0c60fc8ae274c659ebaab002b8736cf
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07176227B2

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