Ethylhydrazine → HCID 21912727, Verbindung

HRID 1357952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1357952
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[CH:15]([CH3:20])[C:16](=O)[CH2:17][CH3:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:22]([NH:24][NH2:25])[CH3:23]>C(#N)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:24]([CH2:22][CH3:23])[N:25]=[C:16]([CH2:17][CH3:18])[C:15]=2[CH3:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 29062EthylhydrazineHCID 18187475HCID 18187475, Verbindung

Produkt 1

HCID 21912727HCID 21912727, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

A solution of 1-(t-butoxycarbonyl)-4-(1,3-dioxo-2-(RS)-methylpent-1-yl)piperidine (435 mg, 1.5 mmol) (from Step D) in 2:1 v/v acetonitrile/water (12 mL) was treated with ethylhydrazine (34% sol'n in water, 0.28 mL, 1.6 mmol) and the resulting mixture was stirred at rt for 20 h. The reaction mixture was partitioned between 75 mL of ether and 25 mL of sat'd sodium chloride and the layers were separated. The organic layer was dried over magnesium sulfate and concentrated. MPLC (Biotage) on a 40S silica cartridge using 4:1 v/v, then 1:1 v/v hexanes/ethyl acetate as the eluent afforded 348 mg (74%) of the title compound:

Aufarbeitung

  1. customThe reaction mixture was partitioned between 75 mL of ether and 25 mL of sat'd sodium chloride
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3e990a87ee854a938eb00f409e6d5041
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593346B2

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