Hydrochloric Acid → (R)-3-pyrrolidin-2-yl-benzoic acid methyl ester hydrochloride

HRID 1524301Notes

Reaction equation

HRID 1524301 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[CH:14]=1)=O)(C)(C)C.[ClH:23].O1CCOCC1>C(Cl)Cl>[ClH:23].[CH3:22][O:21][C:19](=[O:20])[C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)[CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66653196HCID 66653196, compound

Product 1

HCID 66519622(R)-3-pyrrolidin-2-yl-benzoic acid methyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stifling solution of (R)-2-(3-methoxycarbonyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (830 mg, 2.582 mmol) in methylene chloride (30 mL) at room temperature add 4 M HCl in dioxane solution (12.91 mL, 51.64 mmol) and stir the reaction at ambient temp for 18 h. Concentrate the solution in vacuo at 35° C. to remove most solvent. Dilute and stir the dioxane suspension of solids with Et2O (50 mL) and hexane (50 mL). Filter the solid washing with Et2O then hexane and dry in vacuo under P2O5 to give (R)-3-pyrrolidin-2-yl-benzoic acid methyl ester HCl as a solid (577 mg).

Workup

  1. customthe reaction at ambient temp for 18 h
  2. concentrationConcentrate the solution in vacuo at 35° C.
  3. customto remove most solvent
  4. additionDilute
  5. stirringstir
  6. additionthe dioxane suspension of solids with Et2O (50 mL) and hexane (50 mL)
  7. filtrationFilter the solid
  8. washwashing with Et2O
  9. dry with materialhexane and dry in vacuo under P2O5

Sources & evidence

ORD record
ord-fd062f1a420f441293b021a5d5d9321e
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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