Isopropyl iodide → HCID 66854854, compound

HRID 2060793Notes

Reaction equation

HRID 2060793 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:16][CH:15]([OH:17])[CH2:14][CH:13]2[CH2:12][O:11][N:10]3[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:5]=[CH:6][C:7]=1[F:8].I[CH:28]([CH3:30])[CH3:29]>ClCCl.FC(F)(F)S([O-])(=O)=O.[Ag+]>[Br:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:16][CH:15]([O:17][CH:28]([CH3:30])[CH3:29])[CH2:14][CH:13]2[CH2:12][O:11][N:10]3[CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 6362Isopropyl iodideHCID 66853487HCID 66853487, compound

Product 1

HCID 66854854HCID 66854854, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of racemic (3aRS,5RS,6aSR)-6a-(3-bromo-4-fluorophenyl)-1-(4-methoxybenzyl)hexahydro-1H-cyclopenta[c]isoxazol-5-ol (1.72 g, 4.07 mmol) in dichloromethane (2.5 mL) is added silver trifluoromethanesulfonate (2.62 g, 10.2 mmol) and powdered dried 4A sieves (1.50 g). A solution of 2-iodopropane (1.73 g, 10.2 mmol) in dichloromethane (0.5 mL) is added to the mixture over 15 minutes. The thick mixture is stirred at room temperature overnight. The mixture is diluted with dichloromethane and is filtered through diatomaceous earth. The solvent is removed under reduced pressure and the residue is purified by silica gel chromatography with a linear gradient of 0% to 10% ethyl acetate in dichloromethane over 15 minutes to give the title compound (0.466 g, 25%). ES/MS m/e (79Br/81Br) 464, 466 (M+1).

Workup

  1. dry with materialpowdered dried 4A sieves (1.50 g)
  2. filtrationis filtered through diatomaceous earth
  3. customThe solvent is removed under reduced pressure
  4. customthe residue is purified by silica gel chromatography with a linear gradient of 0% to 10% ethyl acetate in dichloromethane over 15 minutes

Sources & evidence

ORD record
ord-6cf20a47b3194f78a66fa04dbfbd7f6f
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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