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Triethanolamine → (R)-1-(4-tert-butoxyphenyl)ethylamine

HRID 2425846
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2425846
[C:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C@H:12]([NH:14]C(=O)COC)[CH3:13])=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].N(CCO)(CCO)CCO.[OH-].[Na+]>O>[C:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C@H:12]([NH2:14])[CH3:13])=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7618TriethanolamineHCID 14798Sodium HydroxideHCID 67255626N-[(1R)-1-(4-tert-Butoxyphenyl)ethyl]-2-methoxyacetamide

Produkt 1

HCID 29003336(R)-1-(4-tert-butoxyphenyl)ethylamineAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

(R)—N-1-(4-tert-Butoxyphenyl)ethylmethoxyacetamide from example 1.3 (180 g with a purity of 94%; corresponds to 0.64 mol of pure substance) was mixed with triethanolamine (20 ml) with stirring and then admixed with 50% NaOH (70.8 g, 0.89 mol). The mixture was then stirred at a bath temperature of 140° C. for another seven hours, after which all of the amide had been converted according to GC. The mixture was diluted with water (100 ml), cooled and extracted with tert-butyl methyl ether (3×100 ml). The combined extracts were washed with saturated sodium chloride solution (50 ml) and dried over Na2SO4. After the solvent had been removed on a rotary evaporator, 123.7 g (73%) of (R)-1-(4-tert-butoxyphenyl)ethylamine were obtained in the form of a pale brownish oil. The chemical purity was 99.4%, the optical purity 98.9% ee.

Aufarbeitung

  1. stirringThe mixture was then stirred at a bath temperature of 140° C. for another seven hours
  2. temperaturecooled
  3. extractionextracted with tert-butyl methyl ether (3×100 ml)
  4. washThe combined extracts were washed with saturated sodium chloride solution (50 ml)
  5. dry with materialdried over Na2SO4
  6. customAfter the solvent had been removed on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-cc9fb6da51cc42da9da4b1c2073b15d1
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07968328B2

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