1,1-Dichloroethane → HCID 58786483, compound

Reaction equation

[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]

Participants

Reactant 4

HCID 63651,1-Dichloroethane

HCID 7912Diisopropylamine

HCID 5049666Sodium triacetoxyborohydride

HCID 58786478HCID 58786478, compound

Product 1

HCID 58786483HCID 58786483, compoundYield 49%

Procedure

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.