Lithium Hydroxide → 1-(tert-Butoxycarbonyl)-4-(4-chlorophenyl)pyrrolidine-3-carboxylic acid

HRID 1992685Notes

Reaction equation

HRID 1992685 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][C@H:9]2[C:20]([O:22]C)=[O:21])=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCCC1>[C:16]([O:15][C:13]([N:11]1[CH2:12][C@@H:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C@H:9]([C:20]([OH:22])=[O:21])[CH2:10]1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59131029HCID 59131029, compound

Product 1

HCID 27621121-(tert-Butoxycarbonyl)-4-(4-chlorophenyl)pyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-tert-butyl 3-methyl (3S,4R)-4-(4-chlorophenyl)pyrrolidine-1,3-dicarboxylate, from preparation 67 (0.98 g, 2.88 mmol) in tetrahydrofuran (8 mL) was added lithium hydroxide (0.21 g, 8.64 mmol) at room temperature. The reaction mixture was stirred for 24 hours and the solvent was removed in vacuo. The crude residue was dissolved in water (8 mL) and 1M hydrochloric acid solution (8.65 mL) was added. The suspension was extracted with dichloromethane (2×40 mL) and the organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo to afforded the desired product as a white solid, 705 mg (75%).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe crude residue was dissolved in water (8 mL)
  3. addition1M hydrochloric acid solution (8.65 mL) was added
  4. extractionThe suspension was extracted with dichloromethane (2×40 mL)
  5. dry with materialthe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b8ab7bacf5e14e9bb7d078022284f9f0
Source dataset
uspto-grants-2010_01
Patent number
US07649002B2

Reaction notes

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