Dichloromethane → HCID 21282679, compound

HRID 414072Notes

Reaction equation

HRID 414072 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]([Br:19])[C:12]=1[O:20]C)[CH3:2].B(Br)(Br)Br.C(Cl)[Cl:28]>>[ClH:28].[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]([Br:19])[C:12]=1[OH:20])[CH3:2]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 54940HCID 54940, compound

Product 1

HCID 21282679HCID 21282679, compound

Procedure

10.0 g (0.025 ml) of (-)-N-ethyl-2-(3-bromo-2,6-dimethoxybenzamidomethyl)pyrrolidine is dissolved in 250 ml of methylene chloride. 2.6 ml (0.027 mol) of boron tribromide is added. The mixture is left over night at room temperature. It is then washed with 2N NH3, dried over Na2SO4 and evaporated after addition of HCl-ether. The residue is dissolved in water and extracted with ether. The water phase is made alkaline with NH3 and is extracted with chloroform. The chloroform phase is dried over Na2SO4 and evaporated. To the residue is added HCl-ether. The salt is filtered off, washed with ether and dried over P2O5. M.p.: sinterring at 100° C. Yield 6.6 g. Hygroscopic [α]D20 =-45.5° (base).

Workup

  1. waitThe mixture is left over night at room temperature
  2. washIt is then washed with 2N NH3
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. additionafter addition of HCl-ether
  6. dissolutionThe residue is dissolved in water
  7. extractionextracted with ether
  8. extractionis extracted with chloroform
  9. dry with materialThe chloroform phase is dried over Na2SO4
  10. customevaporated
  11. additionTo the residue is added HCl-ether
  12. filtrationThe salt is filtered off
  13. washwashed with ether
  14. dry with materialdried over P2O5
  15. customsinterring at 100° C
  16. customHygroscopic [α]D20 =-45.5° (base)

Sources & evidence

ORD record
ord-bb2f19f3b7a24f898c1c1a8f9750c754
Source dataset
uspto-grants-1988_12
Patent number
US04789683

Reaction notes

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