Methanol → 2-(3',4'-Dihydroxybenzyl)-5-(2-phenylethyl) pyrrolidine hydrobromide

HRID 1589370Notes

Reaction equation

HRID 1589370 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23]C)[CH2:6][CH:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:8]1.B(Br)(Br)[Br:26].CO>C(Cl)Cl>[BrH:26].[OH:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[OH:23])[CH2:6][CH:7]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 130650362-(3'4'-Dimethoxybenzyl)-5-(2-phenylethyl)pyrrolidine

Product 1

HCID 130650372-(3',4'-Dihydroxybenzyl)-5-(2-phenylethyl) pyrrolidine hydrobromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (-70° C.) solution of 15.1 g (0.057 mole) of 2-(3',4'-dimethoxybenzyl)-5-(2-phenylethyl)pyrrolidine in 1 L of methylene chloride was added dropwise 55.1 g (0.22 mole) of boron tribromide. After the addition the reaction mixture was gradually warmed up to room temperature over a period of 2 h. 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 dark residue was boiled in ethyl acetate and decanted, then triturated with ethyl acetate and left overnight to give a solid. This was recrystallized twice from acetonitrile to give 6 g. m.p. 149°-151° C.

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. customThis was recrystallized twice from acetonitrile
  10. customto give 6 g

Sources & evidence

ORD record
ord-c4147fe7490b4bce80c3654eb4393da1
Source dataset
uspto-grants-1986_02
Patent number
US04569941

Reaction notes

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