Water → (S)-3-hydroxy-1-(4-methoxyphenethyl)pyrrolidine

HRID 1859445Notes

Reaction equation

HRID 1859445 reaction equation
[N+](C1C=CC(C([O:10][C@H:11]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH2:12]2)=O)=CC=1)([O-])=O.O1CCCC1.O.[Li+].[OH-]>CO>[OH:10][C@H:11]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 69901303(S)-3-(4-Nitrobenzoyloxy)-1-(4-methoxyphenethyl)pyrrolidine

Product 1

HCID 12148702(S)-3-hydroxy-1-(4-methoxyphenethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-3-(4-Nitrobenzoyloxy)-1-(4-methoxyphenethyl)pyrrolidine (1.00 g, 2.70 mmol) was dissolved in methanol (20 ml), tetrahydrofuran (20 ml) and water (10 ml). 4 M-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 then the residue was distributed in water and ether. The organic layer was dried, and the solvent was evaporated under reduced pressure to obtain (S)-3-hydroxy-1-(4-methoxyphenethyl)pyrrolidine in the form of a light yellow oil (541 mg, 91%).

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-cfad9beb32ce42e68e3b879e7d04bdaa
Source dataset
uspto-grants-2003_03
Patent number
US06528504B2

Reaction notes

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