Hydrochloric Acid → 1-(4-iodophenyl)pyrrolidine

HRID 1622665Notes

Reaction equation

HRID 1622665 reaction equation
B.O1CCCC1.[I:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:18][CH2:17][CH2:16][C:15]2=O)=[CH:10][CH:9]=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[I:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 22287313HCID 22287313, compound

Product 1

HCID 112773071-(4-iodophenyl)pyrrolidineYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of borane-tetrahydrofuran complex (1.2 M in THF, 5.81 mL) and 1-(4-iodophenyl)pyrrolidin-2-one (1.00 g) in THF (dry) (20 ml) was stirred at 70° C. under N2 for 3 hr. The mixture was poured into 1N HCl aq., sat. NaHCO3 aq. was added and the mixture was extracted with EtOAc. The organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound (0.954 g) as a white solid.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c2e7bd18f1c948b4ae31fdff2a9803bb
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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