Phenylglyoxal → N-(2-phenyl-2-hydroxyethyl)-4-(N-Boc-2-aminoethyl)aniline

HRID 1351469

Reaktionsgleichung

Reaktionsgleichung von HRID 1351469
[C:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:18]1([C:24]([CH:26]=O)=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[BH3-]C#N.[Na+]>CO>[C:18]1([CH:24]([OH:25])[CH2:26][NH:15][C:14]2[CH:16]=[CH:17][C:11]([CH2:10][CH2:9][NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])=[CH:12][CH:13]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 14090PhenylglyoxalHCID 382207Tert-butyl 4-aminophenethylcarbamateHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 21959862N-(2-phenyl-2-hydroxyethyl)-4-(N-Boc-2-aminoethyl)anilineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

4-(N-Boc-2-aminoethyl)aniline 28 (1.25 g, 5.29 mmole) was dissolved in methanol (30 mL), followed by addition of phenyl glyoxal 24 (0.708 g, 5.28 mmole). The reaction mixture was stirred for 1 h at rt, prior to addition of NaCNBH3 (0.665 g, 10.6 mmole). The final mixture was stirred for 12 h at rt, concentrated, and purified by flash silica column chromatography (2 to 5% MeOH/CH2Cl2) to give N-(2-phenyl-2-hydroxyethyl)-4-(N-Boc-2-aminoethyl)aniline as a pale yellow oil (1.71 g, 91%): Rf=0.18 in 5% MeOH/CH2Cl2. 1H-NMR (CD3OD, 299.96 MHz): δ (ppm) 7.4–7.25 (m, 5H), 7.0–6.95 (d, 2H), 6.63–6.60 (d, 2H), 4.85–4.79 (dd, 1H), 3.3–3.21 (t, 2H), 3.2–3.15 (m, 2H), 2.64–2.5 (t, 2H), 1.42 (s, 9H).

Aufarbeitung

  1. concentrationconcentrated
  2. custompurified by flash silica column chromatography (2 to 5% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-18fc287f6ae74f5d9a25db91e4a9e298
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217738B2

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