Aluminum(III) Chloride → HCID 131729027, compound

HRID 1013374Notes

Reaction equation

HRID 1013374 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[S:14][CH:15]=[C:16]([Br:18])[CH:17]=2)[CH:10]([C:19](Cl)=[O:20])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH2:1]([N:8]1[CH2:12][CH:11]2[CH:10]([C:19](=[O:20])[C:17]3[C:16]([Br:18])=[CH:15][S:14][C:13]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 862291871-Benzyl-4-(4-bromo-thiophen-2-yl)-pyrrolidine-3-carbonyl chloride

Product 1

HCID 131729027HCID 131729027, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product from step d) (4.04 g, 9.59 mmol) in CH2Cl2 (13.7 ml) was added dropwise to a slurry of AlCl3 (3.83 g, 28.77 mmol) in CH2Cl2 (36 ml) at 22° C. After 45 minutes, the reaction mixture was poured into ice cold 2 M NaOH (100 ml) and extracted with CH2Cl2 (300 ml). The organic layer was dried (MgSO4) and solvent evaporated in vacuo to give a residue that was purified by silica-gel chromatography using a ethyl acetate/hexanes gradient (0% to 50% ethyl acetate) to give the subtitle compound (2.4 g, 72%). MS calculated for C16H14BrNOS+H 348, observed 348, 350.

Workup

  1. extractionextracted with CH2Cl2 (300 ml)
  2. dry with materialThe organic layer was dried (MgSO4) and solvent
  3. customevaporated in vacuo
  4. customto give a residue that
  5. customwas purified by silica-gel chromatography

Sources & evidence

ORD record
ord-95f972eee4154b85ac294298dae7c9e9
Source dataset
uspto-grants-2011_07
Patent number
US07981919B2

Reaction notes

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