Sodium Hydroxide → (S)-3-Hydroxy-1-[3-(4-methoxyphenyl)propyl]pyrrolidine

HRID 1859456Notes

Reaction equation

HRID 1859456 reaction equation
[N+](C1C=CC(C([O:10][C@H:11]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH2:12]2)=O)=CC=1)([O-])=O.[OH-].[Na+]>CO>[OH:10][C@H:11]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH2:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69900894(S)-3-(4-nitrobenzoyloxy)-1-[3-(4-methoxyphenyl)propyl]pyrrolidine

Product 1

HCID 57440106(S)-3-Hydroxy-1-[3-(4-methoxyphenyl)propyl]pyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-3-(4-Nitrobenzoyloxy)-1-[3-(4-methoxyphenyl)propyl]pyrrolidine (507 mg, 1.32 mmol) was dissolved in methanol (10 ml). 1 M-NaOH (1.5 ml) was added dropwise in the obtained mixture. After stirring at room temperature for 1 hour, the solvent was evaporated under reduced pressure. The residue was distributed in water and ethyl acetate. The organic layer was dried, and the solvent was evaporated under reduced pressure to obtain (S)-3-hydroxy-1-[3-(4-methoxyphenyl)propyl] pyrrolidine in the form of a light yellow oil (310 mg, 100%).

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-0c25aca0f85d43439320460f5b6d1138
Source dataset
uspto-grants-2003_03
Patent number
US06528504B2

Reaction notes

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