Hydrogen Bromide → HCID 70050390, compound

HRID 1757161Notes

Reaction equation

HRID 1757161 reaction equation
[CH2:1]([C@H:8]1[C@H:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[C:15]([O:21]C)[CH:14]=2)[CH2:11][NH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)[Br:24].Br>C(Cl)Cl>[BrH:24].[CH2:1]([C@H:8]1[C@H:12]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([OH:21])[CH:14]=2)[CH2:11][NH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 25134Boron tribromideHCID 70047968HCID 70047968, compound

Product 1

HCID 70050390HCID 70050390, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.37 g (1.24 mmol) of trans-3-benzyl-4-(3,4-dimethoxyphenyl)pyrrolidine was dissolved in methylene chloride, and 10 ml of a solution of 1M boron tribromide in methylene chloride was added to the resultant solution. The solution was stirred at room temperature for 3 hr. The reaction mixture was concentrated in vacuo. Further, methylene chloride was added to the concentrate and methanol (3 ml) was dropwise added thereto. The mixture was again concentrated in vacuo. This procedure was repeated several times, and a precipitated crystal was recovered by filtration to prepare 70 mg of a hydrobromide as an intended product (yield: 16%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionFurther, methylene chloride was added to the
  3. concentrationconcentrate
  4. additionmethanol (3 ml) was dropwise added
  5. concentrationThe mixture was again concentrated in vacuo
  6. filtrationa precipitated crystal was recovered by filtration

Sources & evidence

ORD record
ord-d81c217aebae43e08fa21645143c26c7
Source dataset
uspto-grants-1995_08
Patent number
US05444083

Reaction notes

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