Hydrochloric Acid → 1-(4-iodophenyl)pyrrolidine

HRID 2035818Notes

Reaction equation

HRID 2035818 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-0072ed97b2bc4f95ae75dfd5015390ab
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

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