Hydrochloric Acid → HCID 70812157, compound

HRID 590670Notes

Reaction equation

HRID 590670 reaction equation
[CH3:1][C@@H:2]1[C@H:6]([CH3:7])[N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:4]([C:15]([O:17]CC)=[O:16])[CH2:3]1.CO.[OH-].[Li+].Cl>C1COCC1.O>[C:11]([O:10][C:8]([N:5]1[C@@H:6]([CH3:7])[C@@H:2]([CH3:1])[CH2:3][C@H:4]1[C:15]([OH:17])=[O:16])=[O:9])([CH3:12])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 86723605HCID 86723605, compound

Product 1

HCID 70812157HCID 70812157, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of rel-(2S,4S,5S)-1-tert-butyl 2-ethyl 4,5-dimethylpyrrolidine-1,2-dicarboxylate in a mixture of THF (70 mL), MeOH (25 mL), and H2O (25 mL) was added lithium hydroxide (1.53 g, 63.7 mmol). The slurry was stirred at room temperature for 2.5 h and at 45° C. for 2 h. The solution was cooled to room temperature and HCl (aqueous, 1N, 70 mL) was added. The organics were concentrated and the resulting aqueous layer was extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4 and concentrated to provide rel-(2S,4S,5S)-1-(tert-butoxycarbonyl)-4,5-dimethylpyrrolidine-2-carboxylic acid (3.08 g, 84%).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. concentrationThe organics were concentrated
  3. extractionthe resulting aqueous layer was extracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-df7cc36458664f548eda9fd255c0bef5
Source dataset
uspto-grants-2016_01
Patent number
US09233974B2

Reaction notes

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