(R)-2-(2-Chlorophenyl)pyrrolidine

Chemical Properties

Flashing point: 107.5 °C . Vapour pressure: 0.0176mmHg at 25°C. (R)-2-(2-Chlorophenyl)pyrrolidine is a chiral molecule whose optical isomer is (S)-2-(2-Chlorophenyl)pyrrolidine.

Physical properties

A colorless crystal

Uses

(R)-2-(2-Chlorophenyl)pyrrolidine can be used as an intermediate for organic synthesis.

Synthesis

To a dry Schlenk flask under nitrogen is added 0.540 g of (R, R)- (+)-ETHYLENE-1, 2- bis (N5-4, 5,6, 7-TETRAHYDRO-L-INDENYL) titanium difluoride and 120 mL of dry THF. To this solution are added under nitrogen in the following order: 2- (2-chlorophenyl)-pyrroline (15 g), phenylsilane (15 g), pyrrolidine (0.48 mL), and MeOH (0.24 mL). The solution is stirred at RT for 48 h, then the mixture is diluted with 350 mL of diethylether and carefully added with vigorous stirring to 1200 mL of 1 M HCI. The aqueous layer is separated and extracted with three portions of diethyl ether (300 mL each). The aqueous layer is made basic with 3M NAOH and extracted with 5 portions of diethyl ether (200 mL each). The combined ether layers are dried over magnesium sulfate and concentrated in vacuo. The residue is purified by vacuum transfer to give (R)-2-(2-Chlorophenyl)pyrrolidine (15 g, 93%) as a colorless oil.