4-Bromobenzyl bromide → HCID 66961148, compound

Diisopropylethylamine (1.57 ml, 9.00 mmol) was added to a solution (15 ml) of 1.50 g (6.00 mmol) of 4-bromobenzyl bromide and 1.11 g (9.00 mmol) of (R)-pyrrolidin-3-ol hydrochloride in dimethylformamide and the mixture was stirred at room temperature for one hr. The solvent was removed by distillation under the reduced pressure. Water and 1 N hydrochloric acid were then added to the residue, and the mixture was washed with ethyl acetate. A 5 N aqueous sodium hydroxide solution and an aqueous sodium hydrogencarbonate solution were added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and was then filtered. The filtrate was concentrated under the reduced pressure to give 1.09 g (yield 71%) of the title compound.

1. customThe solvent was removed by distillation under the reduced pressure
2. additionWater and 1 N hydrochloric acid were then added to the residue
3. washthe mixture was washed with ethyl acetate
4. additionA 5 N aqueous sodium hydroxide solution and an aqueous sodium hydrogencarbonate solution were added
5. extractionthe mixture was extracted with ethyl acetate
6. dry with materialThe extract was dried over anhydrous sodium sulfate
7. filtrationwas then filtered
8. concentrationThe filtrate was concentrated under the reduced pressure

ORD record

ord-092760c553d7494bbf8d78ca14994d80

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879808B2