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-2d363a0679e4444fbbadc9de57bf5d9b

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889730B2