Triphenylphosphine → HCID 18940749, compound

Reaction equation

[Br:1]N1C(=O)CCC1=O.[C:9]([N:16]([CH2:21][CH3:22])[CH2:17][CH2:18][CH2:19]O)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:9]([N:16]([CH2:17][CH2:18][CH2:19][Br:1])[CH2:21][CH3:22])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

Procedure

11 g (0.0618 mol) of N-bromosuccinimide are added in the course of 5 minutes, with stirring, to a solution, which has been cooled to 0° C., of 10.49 g (0.0516 mol) of 3-(N-BOC-ethylamino)-1-propanol and 16.23 g (0.0619 mol) of triphenylphosphine in 160 ml of methylene chloride. The reaction mixture is stirred for a further 30 minutes at 0°-20° C. and is then concentrated by evaporation in vacuo. The dark-colored oily residue is stirred with 200 ml of hexane, whereupon a brown precipitate forms. After filtration and concentration of the filtrate by evaporation in vacuo, the title compound is obtained in the form of an oil, Rf value=0.71 (silica gel/tert-butyl methyl ether).