Iodine → HCID 66684559, compound

HRID 513038Notes

Reaction equation

HRID 513038 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]([NH:13][C:14](=O)[CH3:15])[CH2:10]C=C.II.[C:19]([O-:22])(O)=[O:20].[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+].[CH2:31]1COCC1>O>[C:19]([O:22][CH:15]1[CH2:10][C@H:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[Br:1])[NH:13][CH2:14]1)(=[O:20])[CH3:31]

Participants

7

Reactant 5

HCID 807IodineHCID 8028TetrahydrofuranHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 66684883HCID 66684883, compound

Product 1

HCID 66684559HCID 66684559, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (R)-N-(1-(2-bromo-5-fluorophenyl)but-3-en-1-yl)acetamide (I-46) (1.50 g, 5.24 mmol) in THF (12 mL) was added water (3 mL) followed by iodine (4.0 g, 15.7 mmol). After stirring 6 hours the reaction mixture was poured into a mixture of saturated aqueous NaHCO3 (30 mL) and saturated aqueous Na2S2O3 (25 mL), extracted with EtOAc (2×40 mL), washed successively with saturated aqueous Na2S2O3, water and brine, dried over sodium sulfate and concentrated to dryness to give (5R)-5-(2-bromo-5-fluorophenyl)pyrrolidin-3-yl acetate (I-47) as a pale amber oil, which was used without purification in the next step. MS m/z 302.0, 304.0 (M+1)+.

Workup

  1. extractionextracted with EtOAc (2×40 mL)
  2. washwashed successively with saturated aqueous Na2S2O3, water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-afc18787466b402db40cbfdb1e89d1ef
Source dataset
uspto-grants-2015_08
Patent number
US09102671B2

Reaction notes

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