Benzaldehyde → HCID 69206757, Verbindung

HRID 902053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902053
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([C:14](=[O:16])[NH2:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].ClCCl>ClCCCl>[CH2:17]([N:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH:10]1[C:14](=[O:16])[NH2:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 4

HCID 240BenzaldehydeHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 11042527Tert-butyl 3-carbamoylpiperazine-1-carboxylate

Produkt 1

HCID 69206757HCID 69206757, VerbindungAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

A solution of (RS)-1-(tert-butyloxycarbonyl)-3-carbamoylpiperazine (ref Bruce et al. Syn. Comm. 1995, 2673-84) (25 g, 0.109 mol) and benzaldehyde (11.1 ml, 0.109 mol) in 1,2-dichloroethane (550 ml) was stirred at room temperature for 1.5 h. Sodium triacetoxyborohydride (34.7 g, 0.163 mol) was added in one portion and the resultant stirred for a further 18 h. Dichloromethane (400 ml) was added and the mixture washed with saturated sodium hydrogen carbonate (600 ml). The organic layer was dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 10-70% ethyl acetate in hexane to afford the title compound as a colourless solid (32.4 g, 93%).

Aufarbeitung

  1. washthe mixture washed with saturated sodium hydrogen carbonate (600 ml)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with 10-70% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-06d7e72f47694bc99ee357277893119e
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365077B2

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