Boron tribromide → HCID 13493842, compound
Reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:10](=[O:24])[C:11]1[C:16]([O:17][CH2:18][CH3:19])=[CH:15][CH:14]=[C:13]([Br:20])[C:12]=1[O:21]CC)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:10](=[O:24])[C:11]1[C:16]([O:17][CH2:18][CH3:19])=[CH:15][CH:14]=[C:13]([Br:20])[C:12]=1[OH:21])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
10.0 g (0.023 mole) of (-)-N-ethyl-2-(3-bromo-2,6-diethoxybenzamidomethyl)pyrrolidine is dissolved in 250 ml of methylene chloride. 2.4 ml (0.025 mole) of boron tribromide is added. The mixture is left over night at room temperature and is then washed with 2N NH3. The extract is dried with Na2SO4 and evaporated. The oily residue crystallizes after a while. Petroleum ether is added to the product, which is then filtered off. Yield 7.0 g. M.p. 74°-76° C. [α]D20 =-66.7° (1% acetone).