Benzylethanolamine → (R)-(-)-5-((Benzyl(2-hydroxyethyl)amino)methyl)pyrrolidin-2-one

HRID 2194352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194352
[O:1]=[C:2]1[NH:6][C@@H:5]([CH2:7]OS(C)(=O)=O)[CH2:4][CH2:3]1.[CH2:13]([NH:20][CH2:21][CH2:22][OH:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([N:20]([CH2:7][C@@H:5]1[NH:6][C:2](=[O:1])[CH2:3][CH2:4]1)[CH2:21][CH2:22][OH:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

3

Edukt 2

HCID 4348BenzylethanolamineHCID 13306709(R)-(5-oxopyrrolidin-2-yl)methyl methanesulfonate

Produkt 1

HCID 66865389(R)-(-)-5-((Benzyl(2-hydroxyethyl)amino)methyl)pyrrolidin-2-oneAusbeute 98,3 %

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of (−)-methanesulfonic acid (R)-5-oxo-pyrrolidin-2-ylmethyl ester (10.53 g, 54.5 mmol) and 2-(benzylamino)ethanol (32.58 g, 215.5 mmol) was heated at 130° C. in a microwave oven (Personal Chemistry Emrys™ Optimizer) for 45 minutes. The residue was partitioned between water and DCM, the organic phase was washed with brine, dried (Na2SO4) and evaporated under vacuum. The crude was purified by flash chromatography (DCM/MeOH 95/5 respectively) to afford the title compound as yellow oil (13.3 g, 98% yield).

Aufarbeitung

  1. customThe residue was partitioned between water and DCM
  2. washthe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated under vacuum
  5. customThe crude was purified by flash chromatography (DCM/MeOH 95/5 respectively)

Quellen und Nachweise

ORD-Eintrag
ord-5fa12628e48240a0bb38eb2dee07a9ae
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334286B2

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