4-[3-(Benzhydryl-sulfamoyl)-propyl]-piperazine-1-carboxylic acid tert-butyl ester → Tert-butyl 4-(3-sulfamoylpropyl)piperazine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][S:17](=[O:33])(=[O:32])[NH:18]C(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[Pd+2].[OH-]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][S:17](=[O:32])(=[O:33])[NH2:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
4
Procedure
A suspension of 4-[3-(benzhydryl-sulfamoyl)-propyl]-piperazine-1-carboxylic acid tert-butyl ester (650 mg, 1.37 mmol) and palladium hydroxide (1.154 g, 1.64 mmol, 20% w from Aldrich) in methanol (10 mL) was hydrogenated at room temperature overnight using a Parr apparatus (50 psi). The reaction mixture was filtered through a Celite cake, and the filtrate was concentrated. Purification of the crude residue by flash column chromatography (40 g of silica gel, eluting with methanol and ethyl acetate) gave 4-(3-sulfamoyl-propyl)-piperazine-1-carboxylic acid tert-butyl ester as an off-white solid (334 mg).