Serinol → 2-[(6-Bromo-1,2-benzisoxazol-3-yl)methyl]amino-1,3-propanediol

반응식

[Br:1][C:2]1[CH:12]=[CH:11][C:5]2[C:6]([CH2:9]Br)=[N:7][O:8][C:4]=2[CH:3]=1.[NH2:13][CH:14]([CH2:17][OH:18])[CH2:15][OH:16].CCN(C(C)C)C(C)C>CN(C=O)C>[Br:1][C:2]1[CH:12]=[CH:11][C:5]2[C:6]([CH2:9][NH:13][CH:14]([CH2:17][OH:18])[CH2:15][OH:16])=[N:7][O:8][C:4]=2[CH:3]=1

참가 물질

실험 절차

A solution of 6-bromo-3-bromomethyl-1,2-benzisoxazole (Intermediate 1, 130 mg), serinol (50 mg) and DIPEA (0.05 ml) in DMF (0.2 ml) was stirred at 60° under nitrogen for 3 h. The mixture was partitioned between water and ethyl acetate and the organic layer was washed with water and brine, dried through a hydrophobic filter and concentrated. The residue was purified on a Varian Bond Elut SPE cartridge (silica, 2 g) eluting with dichloromethane followed by dichloromethane-methanol (9:1) to give the title compound as a yellow gum (33 mg).