Methanol → 2-(3',4'-Dihydroxybenzyl)-5-[2-(4-chlorophenyl)ethyl]pyrrolidine hydrobromide

HRID 66475Notes

Reaction equation

HRID 66475 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:23]=1[O:24]C)[CH2:6][CH:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[NH:8]1.B(Br)(Br)[Br:27].CO>C(Cl)Cl>[BrH:27].[OH:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:23]=1[OH:24])[CH2:6][CH:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[NH:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 201642172-(3',4'-Dimethoxybenzyl)-5-[2-(4-chlorophenyl)ethyl]pyrrolidine

Product 1

HCID 201642162-(3',4'-Dihydroxybenzyl)-5-[2-(4-chlorophenyl)ethyl]pyrrolidine hydrobromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (-70° C.) solution of 24.2 g (0.67 mole) of 2-(3',4'-dimethoxybenzyl)-5-[2-(4-chlorophenyl)ethyl]pyrrolidine in 600 cc of methylene chloride was added dropwise 46.5 g (0.186 mole) of boron tribromide. After the addition the reaction mixture was gradually warmed to room temperature over a period of 2 hours. The mixture was cooled again to -70° C. and 300 ml of methanol was carefully added. Solvent was removed in vacuo. An additional 100 ml of methanol was added and removed in vacuo. The gummy residue was boiled in ethyl acetate and decanted, then triturated with ethyl acetate and left in the refrigerator overnight to give a solid. After recrystallization from a minimum amount of methanol there was obtained 7.05 g.

Workup

  1. additionAfter the addition the reaction mixture
  2. temperatureThe mixture was cooled again to -70° C.
  3. customSolvent was removed in vacuo
  4. additionAn additional 100 ml of methanol was added
  5. customremoved in vacuo
  6. customdecanted
  7. customtriturated with ethyl acetate
  8. customto give a solid
  9. customAfter recrystallization from a minimum amount of methanol
  10. customthere was obtained 7.05 g

Sources & evidence

ORD record
ord-e88779703345469098ab3abac7d57d22
Source dataset
uspto-grants-1982_08
Patent number
US04342692

Reaction notes

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