Sodium Hydroxide → (S)-1-(4-chlorophenethyl)-3-hydroxypyrrolidine

HRID 1859464Notes

Reaction equation

HRID 1859464 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][CH2:7][N:8]2[CH2:12][CH2:11][C@H:10]([O:13]C(=O)C3C=CC([N+]([O-])=O)=CC=3)[CH2:9]2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][CH2:7][N:8]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69899690(S)-1-(4-chlorophenethyl)-3-(4-nitrobenzoyloxy)pyrrolidine

Product 1

HCID 69899443(S)-1-(4-chlorophenethyl)-3-hydroxypyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-1-(4-Chlorophenethyl)-3-(4-nitrobenzoyloxy)pyrrolidine (315 mg, 0.84 mmol) was dissolved in methanol (10 ml). 1 M-NaOH (1 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)-1-(4-chlorophenethyl)-3-hydroxypyrrolidine in the form of a light yellow oil (190 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-8f8a469382fb4dfaac012e9d325b1b4a
Source dataset
uspto-grants-2003_03
Patent number
US06528504B2

Reaction notes

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