Water → 2-(tert-butyldimethylsilyloxy)-N-(1-phenylethyl)ethanamine

HRID 2169176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169176
[C:1]1([CH:7]([NH:9][CH2:10][CH2:11][OH:12])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].O>ClCCl>[Si:22]([O:12][CH2:11][CH2:10][NH:9][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8])([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Komponenten

6

Edukt 4

HCID 962WaterHCID 149092-((1-Phenylethyl)amino)ethan-1-olHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531Diisopropylethylamine

Produkt 1

HCID 867258282-(tert-butyldimethylsilyloxy)-N-(1-phenylethyl)ethanamineAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(1-phenylethylamino)ethanol (33) (2.71 g, 16.4 mmol, Eq: 1.00) in dichloromethane (60 ml) were added diisopropylethylamine (2.97 g, 4.01 ml, 23.0 mmol, Eq: 1.4) followed by tert-butyldimethylsilyl chloride (2.72 g, 18.0 mmol, Eq: 1.1) at room temperature under nitrogen atmosphere. The resulting solution was stirred for 16 hrs and then it was poured into water (200 ml). The organic layer was separated, washed with brine, and dried with MgSO4, concentrated, and chromatographed (silica gel, gradient 0 to 10% ethyl acetate-hexane) to obtain 2-(tert-butyldimethylsilyloxy)-N-(1-phenylethyl)ethanamine (34) (oil, 3.75 g, 13.4 mmol, 81.8% yield).

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. customchromatographed (silica gel, gradient 0 to 10% ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-68ba7c02297f4ab081eed934bc364fd6
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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