Boron tribromide → HCID 13493842, compound

HRID 414075Notes

Reaction equation

HRID 414075 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:10](=[O:24])[C:11]1[C:16]([O:17][CH2:18][CH3:19])=[CH:15][CH:14]=[C:13]([Br:20])[C:12]=1[O:21]CC)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:8][NH:9][C:10](=[O:24])[C:11]1[C:16]([O:17][CH2:18][CH3:19])=[CH:15][CH:14]=[C:13]([Br:20])[C:12]=1[OH:21])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 15565720HCID 15565720, compound

Product 1

HCID 13493842HCID 13493842, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.0 g (0.023 mole) of (-)-N-ethyl-2-(3-bromo-2,6-diethoxybenzamidomethyl)pyrrolidine is dissolved in 250 ml of methylene chloride. 2.4 ml (0.025 mole) of boron tribromide is added. The mixture is left over night at room temperature and is then washed with 2N NH3. The extract is dried with Na2SO4 and evaporated. The oily residue crystallizes after a while. Petroleum ether is added to the product, which is then filtered off. Yield 7.0 g. M.p. 74°-76° C. [α]D20 =-66.7° (1% acetone).

Workup

  1. waitThe mixture is left over night at room temperature
  2. washis then washed with 2N NH3
  3. dry with materialThe extract is dried with Na2SO4
  4. customevaporated
  5. customThe oily residue crystallizes after a while
  6. additionPetroleum ether is added to the product, which
  7. filtrationis then filtered off
  8. customM.p. 74°-76° C. [α]D20 =-66.7° (1% acetone)

Sources & evidence

ORD record
ord-92da08ccdfe748b9833b9742c746cfdc
Source dataset
uspto-grants-1988_12
Patent number
US04789683

Reaction notes

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