Hydrazine hydrate (1:1) → tert-butyl N-(2-amino-2-phenylethyl)carbamate

HRID 1186501

Reaktionsgleichung

Reaktionsgleichung von HRID 1186501
[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][CH:9]([N:16]1C(=O)C2C(=CC=CC=2)C1=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].O.NN>C1COCC1.CO>[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][CH:9]([NH2:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 57826431HCID 57826431, Verbindung

Produkt 1

HCID 2771847tert-butyl N-(2-amino-2-phenylethyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of [2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester (23 g, 63 mmol) in THF (180 mL) and MeOH (180 mL) was added 85% hydrazine hydrate (37 mL, 630 mmol) slowly. The resulting mixture was heated to 65° C. for 15 hours. The reaction mixture was cooled to room temperature, then concentrated to dryness. The residue was purified by column chromatography on silica gel (dichloromethane:MeOH, 100:1, 1% NH3 H2O) to give (2-amino-2-phenyl-ethyl)-carbamic acid tert-butyl ester as a white solid. (Yield 7.4 g, 50%). 1H NMR (300 MHz, CDCl3): δ 7.35-7.24 (m, 5H), 4.81 (brs, 1H), 4.08-4.03 (m, 1H), 3.38-3.21 (m, 2H), 1.44 (s, 9H). LC-MS: [M+H]+ 237.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated to dryness
  3. customThe residue was purified by column chromatography on silica gel (dichloromethane:MeOH, 100:1, 1% NH3 H2O)

Quellen und Nachweise

ORD-Eintrag
ord-fae6c86f7dec49d8989dc996fa74f511
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673905B2

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