Hydrochloric Acid → HCID 178527032, compound

HRID 2361559Notes

Reaction equation

HRID 2361559 reaction equation
[Mg].II.Br[CH2:5][CH2:6]Br.Br[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1.[P:20]([O-:27])(OCC)OCC.Cl>O1CCCC1.CC(C)=O.C(OCC)(=O)C.O>[N:15]1([C:12]2[CH:13]=[CH:14][C:9]([PH:20](=[O:27])[C:9]3[CH:14]=[CH:13][C:12]([N:15]4[CH2:6][CH2:5][CH2:17][CH2:16]4)=[CH:11][CH:10]=3)=[CH:10][CH:11]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 78391,2-DibromoethaneHCID 3780918DiethylphosphiteHCID 5462224MagnesiumHCID 70164571-(4-Bromophenyl)pyrrolidine

Product 1

HCID 178527032HCID 178527032, compoundYield 7%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Under a nitrogen stream, a solution of magnesium (9.7 g, 1.0 equivalent), a small amount of iodine and a small amount of 1,2-dibromoethane in tetrahydrofuran (60 mL) was stirred at room temperature for 30 min. A solution of N-(4-bromophenyl)pyrrolidine (90.5 g, 0.400 moL) synthesized in Reference Example 5 in tetrahydrofuran (200 mL) was added at 20° C. to 40° C. over 1 hr, and the mixture was stirred at 40° C. for 40 min. Then, a solution of diethyl phosphite (16.80 g, 0.30 equivalent) in tetrahydrofuran (40 mL) was added to the mixture at 20° C. to 30° C. over 15 min. 6M Hydrochloric acid (60 mL) and water (60 mL) were added to the mixture at −15° C. to 10° C., and then ethyl acetate (200 mL) and acetone (100 mL) were added thereto. The mixture was partitioned, and the organic layer was washed twice with saturated brine (60 mL), dried over anhydrous magnesium sulfate and filtered naturally. Then, the organic layer was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound (2.91 g, pale-yellow white crystals). yield 7%. melting point 199.0° C.

Workup

  1. additionwas added at 20° C. to 40° C. over 1 hr
  2. customThe mixture was partitioned
  3. washthe organic layer was washed twice with saturated brine (60 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered naturally
  6. concentrationThen, the organic layer was concentrated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6d5baf8823a8423caccb4b069a3cc99c
Source dataset
uspto-grants-2014_04
Patent number
US08691718B2

Reaction notes

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