(S)-tert-butyl 3-bromopyrrolidine-1-carboxylate synthesis

Yield:569660-89-5 100%

Reaction Conditions:

with carbon tetrabromide;triphenylphosphine in tetrahydrofuran at 5; for 0.0833333 h;

Steps:

To a 100 mL round bottom flask was added (R)-(-)-N-Boc-3-pyrrolidinol (1.5 g) under an argon atmosphere. CBr₄ (1.5 g) was then added followed by dry THF (50 mL) and the mixture was cooled to 5° C. PPh₃ was then added over 5 min and the progress was followed by TLC. The solid was removed by filtration and washed with ether. The filtrate was concentrated and purified by column chromatography eluting with 1:3 EtOAc:Hx. Yield: 2.3 g (>100%, used without further purification). ¹H-NMR (CDCl₃) δ 4.48 (br s, 1H), 3.82-3.65 (m, 2H), 3.62-3.46 (m, 2H), 2.38-2-18 (m, 2H), 1.46 (s, 9H).

References:

US2007/249672,2007,A1 Location in patent:Page/Page column 21