Lithium hydroxide, monohydrate → (r)-2-(5-Carboxythiophen-2-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 564220Notes

Reaction equation

HRID 564220 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:7][CH:6]=1)=[O:4].O.[OH-].[Li+]>C1COCC1.O>[C:18]([O:17][C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@@H:10]1[C:8]1[S:9][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66758892(R)-tert-butyl 2-(5-methoxycarbonylthiophen-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 66759425(r)-2-(5-Carboxythiophen-2-yl)pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of EXAMPLE 16A (2.8 g) in THF (20 mL) was added lithium hydroxide monohydrate (500 mg) in water (5 mL). The mixture stirred at ambient temperature overnight and partitioned between ethyl acetate and 0.5 M hydrochloric acid. The extract was washed with water, dried over magnesium sulfate, filtered and concentrated.

Workup

  1. custompartitioned between ethyl acetate and 0.5 M hydrochloric acid
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4ef7170899c0467a9f2f31e2b2d03715
Source dataset
uspto-grants-2011_11
Patent number
US08067613B2

Reaction notes

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