1-Benzyl-2-broMoMethyl-pyrrolidine synthesis

Yield: 79%

Reaction Conditions:

with carbon tetrabromide;triphenylphosphine in tetrahydrofuran at 0 - 20; for 16 h;Appel Halogenation;

Steps:

4.1.41 1-Benzyl-2-(bromomethyl)pyrrolidine (52)
In a flask containing carbon tetrabromide (1.7 g, 5.12 mmol) and triphenylphosphine (1.44 g, 5.49 mmol) in anhydrous tetrahydrofuran (5 mL), 1-benzylpyrrolidin-2-yl-methanol (700 mg, 3.66 mmol) was added at 0 °C. The reaction was allowed to stir at rt for 16 h. The solvent was evaporated under vacuum and the crude mixture was purified by column chromatography 1-10% ethyl acetate in hexanes to yield compound 52 (735 mg, 79%). ¹H NMR (CDCl₃) δ 1.55-1.84 (m, 3H), 2.13 (t, J = 10.04 Hz, 1H), 2.20-2.30 (m, 1H), 2.36 (t, J = 10.42 Hz, 1H), 2.75 (d, J = 11.04 Hz, 1H), 3.10 (d, J = 8.78 Hz, 1H), 3.54 (s, 2H), 4.06-4.19 (m, 1H), 7.19-7.39 (m, 5H).

References:

Purohit, Meena K.;Chakka, Sai Kumar;Scovell, Iain;Neschadim, Anton;Bello, Angelica M.;Salum, Norue;Katsman, Yulia;Bareau, Madeleine C.;Branch, Donald R.;Kotra, Lakshmi P. [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 9,p. 2739 - 2752]