Benzylethanolamine → Tert-butyl 2-(benzyl (2-hydroxyethyl)amino)acetate

HRID 517658Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517658
[CH2:1]([NH:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:18]([O:22][C:23](=[O:26])[CH2:24]Br)([CH3:21])([CH3:20])[CH3:19]>CC#N.C(Cl)Cl>[CH2:1]([N:8]([CH2:9][CH2:10][OH:11])[CH2:24][C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 4348BenzylethanolamineHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Produkt 1

HCID 15817339Tert-butyl 2-(benzyl (2-hydroxyethyl)amino)acetateAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of Compound 2 (1.86 g, 12.3 mmol) and potassium carbonate (1.70 g, 12.3 mmol) in CH3CN anhydrous (50 mL) at 0° C. was dropwise added t-Butyl-bromoacetate (2.41 g, 12.4 mmol) over 45 minute. The reaction mixture was gradually warmed to room temperature and stirred for 66 h. The resulting reaction mixture was filtered, and the filtrate was concentrated to give a white oily compound. The residue was then dissolved in CH2Cl2 (50 mL), and the resulting solution was filtered, and the filtrate was concentrated to afford white Compound 4 (2.94 g, 90%), 1H NMR (CDCl3) δ 1.45 (s, 9H), 2.86 (t, 2H), 3.23 (s, 2H), 3.54 to 3.62 (m, 2H), 3.82 (s, 2H), 7.23 to 7.34 (m, 5H); 13C NMR (CDCl3) δ 28.00, 55.27, 26.52, 58.47, 58.84, 81.29, 127.28, 128.36, 128.81, 138.27, 171.02. HRMS (Positive ion FAB) Calcd for C15H24NO3 [M+H]+ m/z 266.3605. Found: [M+H]+ m/z 266.1756.

Aufarbeitung

  1. customat 0° C.
  2. customover 45 minute
  3. customThe resulting reaction mixture
  4. filtrationwas filtered
  5. concentrationthe filtrate was concentrated
  6. customto give a white oily compound
  7. filtrationthe resulting solution was filtered
  8. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-38fd95a8004e4fb997a5f6812feef8dc
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115094B2

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