Boron tribromide → HCID 21282685, compound

HRID 414073Notes

Reaction equation

HRID 414073 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:10](=[O:22])[C:11]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]([Cl:19])[C:12]=1[O:20]C)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[ClH:19].[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:10](=[O:22])[C:11]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]([Cl:19])[C:12]=1[OH:20])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 15565713HCID 15565713, compound

Product 1

HCID 21282685HCID 21282685, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9.1 g (0.025 mole) of (-)-N-ethyl-2-(3-chloro-2,6-dimethoxybenzamidomethyl)pyrrolidine is dissolved in 250 ml of methylene chloride. 2.6 ml (0.027 mole) of boron tribromide is added. The mixture is left over night at room temperature. It is then washed with 2×100 ml of 2N NH3 and 100 ml of water, dried over Na2SO4 and evaporated. The residue is dissolved in diluted HCl and extracted with ether. The water phase is made alkaline with NH3 and is extracted with chloroform. The extract is dried over Na2SO4 and evaporated. The residue is dissolved in ether and HCl-ether is added. The precipitate is filtered off and dried over P2O5. M.p. sinterring at 100° C. Yield 7.4 g [α]D20 =-51.4° (2% ethanol; pH 10.3).

Workup

  1. waitThe mixture is left over night at room temperature
  2. washIt is then washed with 2×100 ml of 2N NH3 and 100 ml of water
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. dissolutionThe residue is dissolved in diluted HCl
  6. extractionextracted with ether
  7. extractionis extracted with chloroform
  8. dry with materialThe extract is dried over Na2SO4
  9. customevaporated
  10. dissolutionThe residue is dissolved in ether
  11. additionHCl-ether is added
  12. filtrationThe precipitate is filtered off
  13. dry with materialdried over P2O5
  14. customsinterring at 100° C
  15. customYield 7.4 g [α]D20 =-51.4° (2% ethanol; pH 10.3)

Sources & evidence

ORD record
ord-09732bec196a45d18fd13a19f21edb8e
Source dataset
uspto-grants-1988_12
Patent number
US04789683

Reaction notes

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