Sodium Hydroxide → HCID 58396225, compound

HRID 1361611Notes

Reaction equation

HRID 1361611 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 ½ 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
  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-a65f378e4fea4c198dbbc95b400db4b5
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

Loading…