Triethylamine → 2-(4-Bromophenyl)-1-(methylsulfonyl)pyrrolidine

To a suspension of 2-(4-bromophenyl)pyrrolidine hydrogen chloride (250 mg, 0.952 mmol) in anhydrous methylene chloride (5 mL) was added triethylamine (0.66 mL, 4.76 mmol) under N2. The mixture was stirred at room temperature for 15 min. under N2. After 15 min., methanesulfonyl chloride (0.31 g, 2.72 mmol) was added and the mixture was stirred at room temperature under N2 overnight. Additional methanesulfonyl chloride (0.29 g, 2.54 mmol) and triethylamine (0.35 mL, 2.38 mmol) were added and stirred at room temperature for 4 h. The reaction was concentrated, and to the residue was added water (20 mL) and methylene chloride (18 mL), and the organic phase was washed with water (10 mL×3), brine (15 mL×1), dried over sodium sulfate and concentrated to afford the desired product (240 mg, 85.2% yield) which was used without further purification in the next step.

1. waitAfter 15 min.
2. stirringthe mixture was stirred at room temperature under N2 overnight
3. stirringstirred at room temperature for 4 h
4. concentrationThe reaction was concentrated
5. additionto the residue was added water (20 mL) and methylene chloride (18 mL)
6. washthe organic phase was washed with water (10 mL×3), brine (15 mL×1)
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated

ORD record

ord-0e3667fa9e59485593a0b975eba84337

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394285B2