Sodium Hydroxide → HCID 58396225, compound

HRID 446263Notes

Reaction equation

HRID 446263 reaction equation
[CH3:1][N:2]([CH3:18])[C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13]C)=[O:12])[CH2:4]1.[OH-].[Na+]>CO>[CH3:1][N:2]([CH3:18])[C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([OH:13])=[O:12])[CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66970375HCID 66970375, compound

Product 1

HCID 58396225HCID 58396225, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-methyl 3-(3-(dimethylamino)pyrrolidin-1-yl)benzoate (0.555 g, 2.24 mmol) in MeOH (2.5 mL) was added 1N NaOH (2.5 mL). The reaction was sealed and heated to 70 deg. C. for 1 h. The reaction was cooled to ambient temperature and was concentrated to % the volume in vacuo. Water was added, followed by 1N HCl until pH 5-6 is obtained. The resulting thick oily mixture was extracted seven times with dichloromethane. The aqueous layer was concentrated in vacuo to a solid, which was rinsed with 1:1 MeOH/MC and filtered. The filtrate was concentrated in vacuo to give (S)-3-(3′-(dimethylamino)pyrrolidin-1-yl)benzoic acid as a yellow solid. MS m/z=235 [M+1]+. Calc'd for C13H18N2O2: 234.29.

Workup

  1. customThe reaction was sealed
  2. temperatureheated to 70 deg. C
  3. concentrationwas concentrated to % the volume in vacuo
  4. additionWater was added
  5. customis obtained
  6. extractionThe resulting thick oily mixture was extracted seven times with dichloromethane
  7. concentrationThe aqueous layer was concentrated in vacuo to a solid, which
  8. washwas rinsed with 1:1 MeOH/MC
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a24158837d8a4ed7b5a8df99c1a061d8
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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