1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) → HCID 86700512, compound

HRID 1500522Notes

Reaction equation

HRID 1500522 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH3:13])[CH2:10][C@H:9]1[C:14]1[NH:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=2)[N:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:26][B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](O)(CC1)CC2>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH3:13])[CH2:10][C@H:9]1[C:14]1[NH:15][C:16]([F:26])=[C:17]([C:19]2[CH:20]=[CH:21][C:22]([Br:25])=[CH:23][CH:24]=2)[N:18]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 27373291-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)HCID 178461444HCID 178461444, compound

Product 1

HCID 86700512HCID 86700512, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2S,4S)-2-[4-(4-bromo-phenyl)-1H-imidazol-2-yl]-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (500 mg, 1.23 mmol) and 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (436 mg, 1.36 mmol) in DMF (20 mL) was stirred at RT for 1 h, concentrated by rotary evaporation, and purified by silica gel chromatography (0-100% EtOAc/hexanes with 1% Et3N). Desired fractions were collected and concentrated to provide the title intermediate (180 mg, 35% yield). (m/z): [M+H]+ calcd for C19H24BrFN3O2 424.10, 426.09 found 424.1.

Workup

  1. concentrationconcentrated by rotary evaporation
  2. custompurified by silica gel chromatography (0-100% EtOAc/hexanes with 1% Et3N)
  3. customDesired fractions were collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2760a6151f1048c58ab2b9586a9eace0
Source dataset
uspto-grants-2015_12
Patent number
US09206159B2

Reaction notes

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