tert-Butyl piperazine-1-carboxylate → HCID 86693013, compound

Reaction equation

[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:14][C:15]1[C:23]2[O:22][CH:21]=[C:20]([CH:24]=O)[C:19]=2[CH:18]=[CH:17][CH:16]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CCOC(C)=O>[Br:14][C:15]1[C:23]2[O:22][CH:21]=[C:20]([CH2:24][N:11]3[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]3)[C:19]=2[CH:18]=[CH:17][CH:16]=1

Participants

Procedure

To a flask charged with Boc-piperazine (130 mg, 0.70 mmol) and 7-bromo-1-benzofuran-3-carbaldehyde (141 mg, 0.63 mmol) was added NaBH(OAc)3 (761 mg, 2.80 mmol). The mixture was stirred at room temperture for 12 hours. Then the reaction was diluted with EtOAc (50 mL), washed with brine (15 mL), dried over Na2SO4 and concentrated. The residue was purified with prep-TLC to obtain the pure product tert-butyl 4-[(7-bromo-1-benzofuran-3-yl)methyl]piperazine-1-carboxylate.