Imidazole → HCID 66862085, compound

A solution of imidazole (310 mg, 4.5 mmol), 1.75 g (6.5 mmol) of triphenylphosphine, and 568 mg (2.2 mmol) of iodine in tetrahydrofuran (12 ml) was added under ice cooling to a solution of 504 mg (1.8 mmol) of (S)-(4-bromophenyl)(2-(hydroxymethyl)pyrrolidin-1-yl)methanone synthesized in step (i) of Reference Example 8 in methylene chloride (40 ml), and the mixture was stirred under ice cooling for 3 hr and then at room temperature for 4 hr. The reaction solution was diluted with 60 ml of ethyl acetate and was washed with an 8% aqueous sodium hydrogencarbonate solution. The aqueous layer was washed twice with 8 ml of ethyl acetate. The organic layers were combined and were washed with 25% brine. The organic layer was dried over anhydrous sodium sulfate and was filtered. The filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give 438 mg (yield 63%) of the title compound.

1. waitat room temperature for 4 hr
2. washwas washed with an 8% aqueous sodium hydrogencarbonate solution
3. washThe aqueous layer was washed twice with 8 ml of ethyl acetate
4. washwere washed with 25% brine
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
6. filtrationwas filtered
7. concentrationThe filtrate was concentrated under the reduced pressure
8. customthe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1)

ORD record

ord-06f17ccddb66469495b50ed8a33118d5

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07871982B2