Hydrochloric Acid → 1-(4-iodophenyl)pyrrolidine

HRID 1747932Notes

Reaction equation

HRID 1747932 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. extractionthe mixture was extracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a0f5fb8e92b46e59141d15a3b13bf21
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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