Hydrochloric Acid → 1-(tert-Butoxycarbonyl)-4-(4-chlorophenyl)pyrrolidine-3-carboxylic acid

HRID 2047455Notes

Reaction equation

HRID 2047455 reaction equation
C([C@@H]1COC(=O)N1C([C@H:16]1[C@H:20]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH2:19][N:18]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:17]1)=O)C1C=CC=CC=1.[OH-].[Li+].[C:37]([O:40]CC)(=[O:39])C.Cl>C1COCC1.O>[C:31]([O:30][C:28]([N:18]1[CH2:19][C@@H:20]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[C@H:16]([C:37]([OH:40])=[O:39])[CH2:17]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 67231025HCID 67231025, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of the compound (17.0 g) obtained in step 4 in THF (60 mL) and water (15 mL) was added at 0° C. 4N lithium hydroxide (35.1 mL), and the mixture was stirred at room temperature for 16 hr. To the reaction mixture was added ethyl acetate, and the mixture was acidified with 2N hydrochloric acid. The organic layer was dried, and the solvent was evaporated under reduced pressure to give (3S,4R)-1-(tert-butoxycarbonyl)-4-(4-chlorophenyl)pyrrolidine-3-carboxylic acid (7.35 g) as a white powder.

Workup

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

Sources & evidence

ORD record
ord-2c319b4f952f44d1b6e18a6dd73cdedd
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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