Hydrochloric Acid → (+/-)-2'-Oxo-3,4-dihydro-1H-spiro[naphthalene-2,3'-pyrrolidine]-6-carboxylic acid

HRID 133125Notes

Reaction equation

HRID 133125 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:16]([O:18]C)=[O:17])[CH:12]=3)[CH2:7]2)[CH2:5][CH2:4][NH:3]1.[OH-].[Li+].Cl>C1COCC1.O>[O:1]=[C:2]1[C:6]2([CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:16]([OH:18])=[O:17])[CH:12]=3)[CH2:7]2)[CH2:5][CH2:4][NH:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67526846(+/-)-Methyl 2'-oxo-3,4-dihydro-1H-spiro[naphthalene-2,3'-pyrrolidine]-6-carboxylate

Product 1

HCID 59027884(+/-)-2'-Oxo-3,4-dihydro-1H-spiro[naphthalene-2,3'-pyrrolidine]-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of (±)-methyl 2′-oxo-3,4-dihydro-1H-spiro[naphthalene-2,3′-pyrrolidine]-6-carboxylate from Step F (50 mg, 0.193 mmol) and lithium hydroxide (24 mg, 0.578 mmol) in THF (3 mL) and H2O (1 mL) was heated at reflux for 5 h, then allowed to cool. The mixture was poured into 10% aqueous HCl (10 mL) and extracted with EtOAc (3×20 mL), and the combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was triturated with CH2Cl2 to give the title compound. MS: m/z=246 (M+1).

Workup

  1. temperatureat reflux for 5 h
  2. temperatureto cool
  3. extractionextracted with EtOAc (3×20 mL)
  4. dry with materialthe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with CH2Cl2

Sources & evidence

ORD record
ord-f9bcebe5b05e4182bd1e7c8e554252de
Source dataset
uspto-grants-2008_06
Patent number
US07390798B2

Reaction notes

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