Pyridine → tert-butyl (2S)-2-(bromomethyl)pyrrolidine-1-carboxylate

To a solution of N-bromosuccinimide (1.33 g, 7.45 mmol, 3 eq) in DCM (15 ml) was added drop wise a solution of triphenylphosphine (1.82 g, 6.94 mmol, 2.8 eq) in DCM (15 ml). The solution was stirred at room temperature for 15 minutes. Pyridine (0.015 ml, 1.2 eq) was added followed by dropwise addition of (R)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.50 g, 2.48 mmol, 1 eq) in DCM (15 ml). The solution was stirred overnight at room temperature. The solvent was removed under reduced pressure. The residue was triturated in diethyl ether (2×5 0 ml) and 10% ethyl acetate in heptane. The solvents from trituration were combined and concentrated under reduced pressure to give a pale pink solid. The product was purified using column chromatography eluting with ethyl acetate/heptane to give the title compound (0.20 g, 30% yield).

1. stirringThe solution was stirred overnight at room temperature
2. customThe solvent was removed under reduced pressure
3. customThe residue was triturated in diethyl ether (2×5 0 ml)
4. concentrationconcentrated under reduced pressure
5. customto give a pale pink solid
6. customThe product was purified
7. washeluting with ethyl acetate/heptane

ORD record

ord-2db419cf30f14e618f2d6bdfa85236fa

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08148531B2