Water → (S)-1-(4-dimethylaminophenethyl)-3-hydroxypyrrolidine

HRID 1859451Notes

Reaction equation

HRID 1859451 reaction equation
[CH3:1][N:2]([CH3:28])[C:3]1[CH:27]=[CH:26][C:6]([CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][C@H:11]([O:14]C(=O)C3C=CC([N+]([O-])=O)=CC=3)[CH2:10]2)=[CH:5][CH:4]=1.O1CCCC1.O.[Li+].[OH-]>CO>[CH3:28][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10]2)=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 69900132(S)-1-(4-Dimethylaminophenethyl)-3-(4-nitrobenzoyloxy)pyrrolidine

Product 1

HCID 69900648(S)-1-(4-dimethylaminophenethyl)-3-hydroxypyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-1-(4-dimethylaminophenethyl)-3-(4-nitrobenzoyloxy) pyrrolidine (1.00 g, 2.70 mmol) was dissolved in methanol (20 ml), tetrahydrofuran (20 ml) and water (10 ml). 4M-LiOH (3 ml) was added dropwise in the obtained solution, and they were stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and the residue was distributed in water and ether. The organic layer was dried and the solvent was evaporated under reduced pressure to obtain (S)-1-(4-dimethylaminophenethyl)-3-hydroxypyrrolidine in the form of a light yellow solid (320 mg, 62%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe organic layer was dried
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3e0bbd1f0c324a2d880f4166b09ccf86
Source dataset
uspto-grants-2003_03
Patent number
US06528504B2

Reaction notes

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