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Methanol → 5-Chloro-alpha-(2-tert-butoxycarbonylaminomethylphenyl)-2-neopentylaminobenzyl alcohol

HRID 275845
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 275845
CO.[NH2:3][C:4]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:5]=1[CH:6]([OH:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[CH3:28][C:29]([CH3:33])([CH3:32])[CH:30]=O.C([BH3-])#N.[Na+]>C(OC(=O)C)C.C(O)(=O)C>[Cl:27][C:24]1[CH:25]=[CH:26][C:4]([NH:3][CH2:28][C:29]([CH3:33])([CH3:32])[CH3:30])=[C:5]([CH:23]=1)[CH:6]([OH:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][NH:14][C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 887MethanolHCID 12417PivalaldehydeHCID 5003444Sodium cyanoborohydrideHCID 539893822-Amino-5-chloro-alpha-(2-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

Produkt 1

HCID 542161415-Chloro-alpha-(2-tert-butoxycarbonylaminomethylphenyl)-2-neopentylaminobenzyl alcoholAusbeute 102,2 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a methanol (5 ml) solution of 2-amino-5-chloro-α-(2-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.5 g) were added trimethyl acetaldehyde (132 mg) and acetic acid (92 mg). The mixture was stirred for 10 minutes at room temperature, to which was added sodium cyano borohydride (97 mg), followed by stirring for one hour at room temperature. To the reaction mixture was added acetic acid ethyl ester (50 ml). The mixture was washed with water and dried over anhydrous Na2SO4. The solvent was then distilled off. The residue was purified by means of a silica gel column chromatography to give the object 5-chloro-α-(2-tert-butoxycarbonylaminomethylphenyl)-2-neopentylaminobenzyl alcohol (0.61 g) as a colorless oily product.

Aufarbeitung

  1. stirringby stirring for one hour at room temperature
  2. washThe mixture was washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. distillationThe solvent was then distilled off
  5. customThe residue was purified by means of a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fd5d7ef9b4264046b14cd5f208a34ba8
Quelldatensatz
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06352982B1

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