Triethylamine → Tert-butyl N-(3-oxo-1-phenylpropyl)carbamate

HRID 659129

Reaktionsgleichung

Reaktionsgleichung von HRID 659129
[OH:1][CH2:2][CH2:3][CH:4]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C>CS(C)=O>[C:14]([O:13][C:12](=[O:18])[NH:11][CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][CH:2]=[O:1])([CH3:17])([CH3:15])[CH3:16]

Komponenten

4

Edukt 2

HCID 8471TriethylamineHCID 21803951Tert-butyl (3-hydroxy-1-phenylpropyl)carbamate2×

Produkt 1

HCID 15087934Tert-butyl N-(3-oxo-1-phenylpropyl)carbamateAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 1.63 g of tert-butyl 3-hydroxy-1-phenylpropylcarbamate (Formula 11) in 15 mL of dimethyl sulfoxide (DMSO) was added 2.72 mL of triethylamine. The solution was cooled to 0° C. and 3.1 g of sulfur trioxide pyridine complex in 15 mL of DMSO was added. The reaction mixture was stirred at room temperature for 1 hour then poured onto ice-water and extracted with ethyl acetate. The combined ethyl acetate layers were washed with 10% acetic acid, water, 5% sodium bicarbonate, and brine, dried over sodium sulfate and concentrated. Column chromatography (40% ethyl acetate/hexane) gave 1.2 g (74%) of tert-butyl-3-oxo-1-phenylpropylcarbamate (Formula 12) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.43 (s, 9H), 2.89-2.96 (m, 2H), 5.23 (br, 1H), 5.32 (br, 1H), 7.27-7.37 (m, 5H), 9.74 (m, 1H).

Aufarbeitung

  1. additionthen poured onto ice-water
  2. extractionextracted with ethyl acetate
  3. washThe combined ethyl acetate layers were washed with 10% acetic acid, water, 5% sodium bicarbonate, and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3439144357c24a92953e7c576f236e9f
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080570B2

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