1,1-Dichloroethane → HCID 58786483, Verbindung

Reaktionsgleichung

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:23]([NH:26][CH:27]([CH3:29])C)(C)C.C(O[BH-](O[C:40](=O)[CH3:41])OC(=O)C)(=O)C.[Na+].Cl[CH:45](Cl)C>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][N:26]([CH2:23][CH2:40][CH3:41])[CH2:27][CH2:29][CH3:45])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

Edukt 4

HCID 63651,1-Dichloroethane

HCID 7912Diisopropylamine

HCID 5049666Sodium triacetoxyborohydride

HCID 58786478HCID 58786478, Verbindung

Produkt 1

HCID 58786483HCID 58786483, VerbindungAusbeute 49 %

Versuchsvorschrift

To 4-(2-Oxo-1-phenyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (206) (0.47 g, 1.56 mmol) in dichloroethane (5 mL) was added diisopropylamine (0.21 mL, 1.56 mmol) and sodium triacetoxyborohydride (0.45 g, 2.15 mmol). The reaction was allowed to stir at room temperature for 18 h. The reaction mixture was then quenched with 5N NaOH (5.6 mL) and diluted with EtOAc. The organic phase was dried with MgSO4 and concentrated to dryness. The crude material was purified by chromatography (silica gel 60 mesh, eluting with 100% EtoAc) yielding 0.30 g (49%) pure product.